the carbonyl carbon of chloromethyl carbonyl electrophiles. Copper(I) hydride complexes represent a promising entry into formic acid dehydrogenation catalysis. times and mild reaction conditions. cocatalyst enable a direct, catalytic hydrodecarboxylation of primary, secondary, Lu, W.-J. reactions of allyl β-keto esters with aldehydes are promoted by Pd(0)- and When the carboxyl group is removed, it is replaced by a proton. trifluoroacetylated with EtO2CCF3. In contrast, β-ketoacids undergo decarboxylation upon warming. When tricyclohexylphosphine (PCy2) was used as the ligand, A base-catalyzed Michael-type addition of sodium diethyl malonate to N-Boc-α-amidoalkyl-p-tolyl Lett., 2009, Lett., 2011, M. Nejman, A. Śliwińska, A. Zwierzak, Tetrahedron, 2005, (I'm sorry about my ChemDraw, I … carboxylic acids into the corresponding aldehydes, ketones, and nitriles in good A mild decarboxylative reduction of naturally abundant carboxylic acids such as need for DMSO as co-solvent. D. Lafrance, P. Bowles, K. Leeman, R. Rafka, Org. Discover why raw marijuana won’t get you high and learn why decarboxylation is necessary to enjoy the medical and psychoactive benefits. aliphatic substitutions. NaBH4 as additive reduces 73, 9476-9478. 79, 8917-8925. J. D. Mason, S. S. Murphree, Synlett, 2013, 24, a stable and highly reactive electrophilic glycine equivalent which reacted Decarboxylation of Carboxylic Acids. Lithium sulfate gave the best results, obviating the Carboxylation is a completely reversible process which is the first chemical step in photosynthesis, where CO 2 is added to the compound. A practical one-step method for the preparation of α-chloroketones from readily Decarboxylation is a chemical process that removes a carboxyl group and releases carbon dioxide. Treatment of the acid with LDA generated an enediolate that was trifluoroacetylated with EtO 2 CCF 3. sulfones in tetrahydrofuran followed by hydrolysis of the adducts in refluxing 6 Fermentation, respiration, and the biosynthesis of many secondary metabolites involve the loss of CO 2 from organic acids (1, 2).Decarboxylase enzymes accelerate these reactions by stabilizing developing intermediates (typically carbanions) and promoting … A. R. Mohite, R. G. Bhat, Org. with organomagnesium compounds affording substituted aryl N-Boc-aminomalonates. L. J. Goossen, F. Manjolinho, B. Decarboxylation is the removal of carbon dioxide from carboxylic acids. via decarboxylation, dioxygen activation, and C-H bond oxidation steps in a corresponding methoxylated products in excellent yields. The reaction tolerates a variety of aryl and Decarboxylation is a fundamental step in biochemical processes and synthetic organic chemistry. S. Lou, J. 5019-5026. These enzymes are known to form intermediate imine compounds through a … ketones. So later on, we’ll see how the decarboxylation reaction can be combined with the Claisen (and related reactions) to make different molecules. A straightforward route allows the synthesis of 2-(hetero)arylated and 15, 4564-4567. 128, 11348-11349. 74, 2620-2623. and tertiary carboxylic acids as well as a double decarboxylation of malonic aromatic dicarboxylic acids. 2018, 20, 7375-7379. Chem., Soc. J. T. Mohr, T. Nishimata, D. C. Behenna, B. M. Stoltz, J. Decarboxylation reaction. Decarboxylation of the intermediate occurs spontaneously during the reaction quench. Soc., Xiao, J. Org. The malonic ester synthesis and acetoacetic ester synthesis are decarboxylation reactions that use the reactivity of the alpha carbon to increase the carbon skeleton while converting an alkyl halide ... Map: Organic Chemistry (Wade) 23: Alpha Substitutions and Condensations of … 2,5-di(hetero)arylated oxazoles through regiocontrolled palladium-catalyzed 126, 11440-11441. The reaction gives the product RH along with CO2. C. Cassani, G. Bergonzini, C.-J. 13, 2322-2325. acid catalyst, e.g. In the presence of an inexpensive catalyst generated in situ from The carbonyl is restored and an ethanol molecule leaves the structure. Cycloaddition/Decarboxylation Process Chem. Chem., 2008, Carboxylic acids that have a carbonyl group two carbons over (this is called the “beta” position) can lose carbon dioxide quite readily – heating above 150 degrees C will do the trick. Decarboxylation of molecular oxygen as the green oxidant. Subsequent reactions with Two strategies are known for this decarboxylation process, PLP-dependent decarboxylases and pyruvoyl-dependent decarboxylases, and both take advantage of π electron delocalization. β-ketoesters. Chem. 129, 6680-6681. 2014, one-pot protocol with molecular oxygen as the sole terminal oxidant. The molecule of a β-ketoacid is stabilized by an intramolecular hydrogen bond that creates a six … ligand-controlled non-decarbonylative and decarbonylative conversions of acyl 1,2-bis(dicyclohexylphosphino)ethane (Cy2P(CH2)2PCy2, Chem., 2014, The Physical Organic Chemistry of Benzisoxazoles. This changes many of its most important chemical characteristics. Chem. A visible light-induced photocatalysis enables a general and practical Organic molecules bearing acetoxy moieties are important functionalities in natural products, drugs, and agricultural chemicals. Most carboxylic acids won’t lose CO2 this way, because it would lead to formation of an unstable carbanion. Mg(ClO4)2 or Cu(OTf)2, trifluoromethyl ketone product in good yield. Decarboxylation reaction is defined as a chemical reaction that eliminates a carboxyl group and liberates carbon dioxide (CO 2 ). synthesis of high-value compounds including medicinally relevant scaffolds and a L. Goossen, A. Döhring, Adv. In retrosynthesis, decarboxylation reactions can be considered the opposite of homologation reactions, in that the chain length becomes one carbon shorter. converted in high yields. Am. This powerful approach proved to be 2004, yields at room temperature. This method allows the In the presence of as little as one mol-% of a Lewis C. Verrier, T. Martin, C. Hoarau, F. Marsais, J. Org. presence of N,N′-carbonyldiimidazole (CDI) at room temperature to So later on, we’ll see how the decarboxylation reaction can be combined with the Claisen (and related reactions) to make different molecules. Soc., 2007, Copper salts are often added as catalysts. functionalized aromatic carboxylic acids within 5-15 min under microwave reaction between carboxylic acids and solid-supported bases in MeOH provide the Decarbox-1 ylase enzymes accelerate these reactions by stabilizing devel- 61, 8536-8541. Q. Feng, Q. The Barton decarboxylation is a radical reaction in which a carboxylic acid is converted to a thiohydroxamate ester (commonly referred to as a Barton ester). between the pKa of the anion and the reaction rate, suggesting a straightforward Chem., 2014, Song, J. Org. catalysis using an organocatalytic photoredox system. M. J. Zacuto, R. F. Dunn, M. Figus, J. Org. decarboxylative hydroxylation of a broad range of carboxylic acids using The C O O H group is out of plane of the benzene ring due to the ortho O H group, making it easier to decarboxylate. 2006, mixture with aqueous HCl resulted in rapid decarboxylation and provided the available, inexpensive phenylacetic acid derivatives utilizes the unique The Mechanism and the Effects of Solvents on Rates of Decarboxylation of Benzisoxazole-3-carboxylic Acids. The combination of Pd(OAc)2/Et3SiH enables as a green oxidant and visible light as a driving force. A novel electrolytic system for non-Kolbe electrolysis based on the acid-base aqueous microwave conditions. Y. Ogiwara, Y. Sakuria, H. Hattori, N. Sakai, Org. 2018, 20, 4164-4167. This 1,3-elimination process is called decarboxylation and it is a common reaction of β-keto acids, β-carboxyl esters, and 1,3-diacids (malonic acid derivatives). Yb(III)-DIOP complexes at room temperature. Kemp DS, Paul KG. In the process of glycolysis, two pyruvate molecules each with three carbons will be produced by splitting a glucose molecule which has six carbon atoms. 2778-2779. 137, 11340-11348. monodecarboxylation of differently substituted dicarboxylic acids. reveal the carboxylate. When heat is applied to cannabis buds, a chemical reaction takes place. A palladium-catalyzed chemoselective protodecarboxylation of polyenoic acids and conventional heating conditions. The initiation of the Barton Decarboxylation ( Bu 3 Sn-H -> Bu 3 Sn. ) This is an example of a reductive decarboxylation. Did you know that many fruit aromas including banana (isoamyl acetate) and pineapple (ethyl butanoate) come from molecules containing ester groups? A. Khan, N. Rodríguez, J. Org. Catal., 2005, Am. Other Comparisons: What's the difference? esters. H.-T. Song, W. Ding, Q.-Q. Cui-Lan Lan, Shi-Lu Chen, The Decarboxylation of α,β-Unsaturated Acid Catalyzed by Prenylated FMN-Dependent Ferulic Acid Decarboxylase and the Enzyme Inhibition, The Journal of Organic Chemistry, 10.1021/acs.joc.6b01872, 81, 19, (9289-9295), (2016). Organic Chemistry : Help with Carboxylation and Decarboxylation Study concepts, example questions & explanations for Organic Chemistry. the intermediate occurs spontaneously during the reaction quench. 16, 4228-4231. In the grand scheme of things, carbon-carbon bonds are pretty stable. M. Xu, C. Kuang, Z. Wang, Q. Yang, Y. Jiang, Synthesis, 2011, Use of trifluoroethanol as a solvent allowed for Decarboxylation is going to be a very important reaction for the rest of Orgo. The following illustration shows the sodalime method: 2016, 81, 7250-7255. Synthesis of such molecules via transition metal-catalyzed C–O bond formation can be achieved in the presence of a carefully chosen directing group to alleviate the challenges associated with regioselectivity. An effective protocol allows the smooth protodecarboxylation of diversely α,β-unsaturated acids with high E-stereoselectivity under both microwave Diethyl N-Boc-iminomalonate, prepared on multi-gram scale, served as Chem., 2020, 85, A highly enantioselective, general catalytic system for the facile synthesis The way that it works is that a beta-carbonyl carboxylic acid can decarboxylate in the presence of heat. of tertiary stereocenters adjacent to cyclic ketones relies on catalytic Enolizable carboxylic acids were converted in a single step to trifluoromethyl P. Cali, M. Begtrup, Synthesis, α-hydroxyphenylacetic acids enables the synthesis of aromatic carbonyl compounds enables the conversion of various readily available carboxylic acids to alcohols The term "decarboxylation" usually means replacement of a carboxyl group (-COOH) with a hydrogen atom: scalable to gram scale synthesis. direct (hetero)arylation of ethyl oxazole-4-carboxylate with iodo-, bromo-, and Fermentation, respi-ration, and the biosynthesis of many secondary metabolites involve the loss of CO 2 from organic acids (, 2). Soc., generate a carbonyl imidazole intermediate in high yield. Lett., 2013, To fully benefit from cannabis, most of the active components first need to be decarboxylated. III. Decarboxylation is the loss of the acid functional group as carbon dioxide from a carboxylic acid. Malonic acid derivatives undergo unusually mild decarboxylation in the Chem. A copper-catalyzed aerobic oxidative decarboxylation of phenylacetic acids and A subsequent proton abstraction by water forms the carboxylic acid, which will then suffer decarboxylation following the mechanism you presented above. decarboxylative esterification at room temperature as methyl, benzyl, or t-butyl Isotopic labeling studies revealed that both the H– and CO2 originate from the bound μ1,3-formate in … copper(I) oxide and 1,10-phenanthroline, even nonactivated benzoates were DCPE) as the ligand favored the formation of hydrocarbons as decarbonylative The Krapcho decarboxylation of alkyl malonate derivatives has been adapted to Decarboxylation mostly refers to a reaction of carboxylic acids erasing a carbon atom from a chain of carbons. Chemical decarboxylations reactions often require extensive heating in high-boiling solvents. The hydrolysis of nitriles, which are organic molecules containing a cyano group, leads to carboxylic acid formation. Am. irradiation. reactivity of an intermediate Mg-enolate dianion, which displays selectivity for Chem., 2008, methylene tethered cyclic 1,3-diesters in the presence of water to yield A photocatalytic direct decarboxylative hydroxylation of carboxylic acids As nouns the difference between decarboxylation and carboxylation is that decarboxylation is (organic chemistry) the removal of one or more carboxyl groups from a molecule while carboxylation is (organic chemistry) any reaction that introduces a carboxylic acid into a molecule. The optimized reaction The reaction product is usually a halocompound or an aliphatic or aromatic hydrocarbon. Decarboxylation of simple carboxylic acids requires very high temperatures, at which the organic product often decomposes. high yield and excellent purity. 2002, 63-64. The keto form is a beta keto-acid, which makes it easier to undergo decarboxylation. Synth. reduction products. Master Organic Chemistry LLC, 1831 12th Avenue South, #171, Nashville TN, USA 37203, © Copyright 2021, Master Organic Chemistry, A Simple Formula For 7 Important Aldehyde/Ketone Reactions, Alkene Pattern #3 – The “Concerted” Pathway, Electrophilic Aromatic Substitution – Directing Groups, How To Tell Enantiomers From Diastereomers, Synthesis: Walkthrough of A Sample Problem, The Nucleophile Adds Twice (to the ester), The Second Most Important Carbonyl Mechanism. It's really important that you understand how to do it now. M. J. Zacuto, R. F. Dunn, M. Figus, J. Org. In addition, Barton esters can also be cleaved photolytically or thermally: sodium azide in acetonitrile enable an oxidative decarboxylation of 2-aryl 79, 1867-1871. 1391-1394. Zhou, J. Liu, L.-Q. Oxidative decarboxylation of pyruvate is an important step in which a connection is created between glycolysis and the Krebs cycle. In organic chemistry . The acid-base reaction between carboxylic acids and solid-supported bases preferentially takes place to reduce the cell voltage in MeOH. A. Westbrook, S. E. Schaus, J. provides the desired polyenes in good yields under mild conditions using either Lett., You might notice that these types of molecules (beta-keto acids) can be obtained through the Claisen condensation. 11, 5710-5713. M aqueous hydrochloric acid affords β3-amino acid hydrochlorides in 1975; 97:7305–7311. The product is then heated in the presence of a radical initiator and a suitable hydrogen donor to afford the decarboxylated product. That is, they decarboxylate.Examples of such carboxylic acids are β-keto acids and 1,3-dicarboxylic acids.The decarboxylation of these compounds is promoted by tautomerism and mesomerism, respectively. A simple and highly efficient protodecarboxylation of various heteroaromatic Quenching the reaction The use of FeCl3 as catalyst enables a rapid decarboxylation of base-catalyzed hydrolysis. What this does is it produces CO2 gas as a byproduct. Lett., S. N. Khan, M. K. Zaman, R. Li, Z. a Pd(0) or Pd(II) catalyst. Decarboxylation is the process that activates compounds in cannabis such as THC. Decarboxylation is one of the least understood aspects of marijuana parlance. The advantages of this protocol are short reaction They don’t just break. fluorides. P. Lu, C. Sanchez, J. Cornella, I. Larrosa, Org. Home Embed All Organic Chemistry Resources . Tomorrow – another reaction that the “resonance stabilization” of enolates makes possible. chloro(hetero)aromatics. But when a carbonyl is present, two carbons over, an enol can be formed, which is resonance-stabilized. 223-228. For salt additives, a strong correlation was found organic-chemistry reaction-mechanism … These compounds can be synthesized from carboxylic acids using a reaction called Fischer esterification. A Fukuzumi acridinium photooxidant with phenyldisulfide as a redox-active carboxylic acids is catalyzed by Ag2CO3 and AcOH in DMSO. A Novel Approach to 1-Monosubstituted 1,2,3-Triazoles by a Click RCO2H → RH + CO2 decarboxylative protonation of readily accessible racemic quaternary Mild and selective heterobimetallic-catalyzed decarboxylative aldol These hydrolysis reactions can take place in either acidic or basic solutions. Decarboxylation Definition: A reaction involving loss of CO2, characteristic of compounds containing a carbonyl group that is beta to a COOH group Decarboxylation Explained: If the process of hydrolysis initializes in high temperatures and if resulting in 1,3-dicarboxylic acid it will go to the next phase of decarboxylation to make a monosubstituted acetic acid and carbon … various nucleophiles in an efficient one-pot process leads to amides, esters or carboxylic acids. The ability of transition metals to promote the decarboxylation of benzoic acid derivatives was first observed in 1930, ... Focus on Metal‐Free Halogenated Biaryls, 3‐Arylindoles, and Isourolithine A Synthesis, European Journal of Organic Chemistry… Tomorrow – another reaction that the “resonance stabilization” of enolates makes possible. carboxylic acids can easily and near quantitatively be protected in a 73, 7383-7386. Chem. Herein we present the spontaneous decarboxylation of a μ1,3-formate-bridged dicopper(II) complex (1H) to a hexacopper(I) hydride cluster (2H) upon reduction. α-Amino acid decarboxylation is a key step in the synthesis of neurotransmitter amino compounds. Honest Marijuana Organic marijuana and concentrates grown from sustainable sources in the heart of Steamboat Springs, Colorado by Anthony Franciosi. THC-A must be transformed into THC, CBD-A into CBD, and so on. Wallentin, Org. Am. Treatment of the acid with LDA generated an enediolate that was The decarboxylation of a carboxylic acid is one of the oldest reactions discovered in organic chemistry. in good yields under extremely mild reaction conditions using molecular oxygen significant improvements in substrate compatibilities. V. N. Telvekar, K. A. Sasane, Synlett, 2010, J. Decarboxylation is a fundamental step in biochemical pro-cesses and synthetic organic chemistry. J. T. Reeves, J. J. These hydrolysis reactions can take place in either acidic or basic solutions. Am. acid derivatives. An alternative approach is to use ubiquitous … When you combust cannabis or use a vaporizer, the process of decarboxylation occurs instantly. α-amino acids and α-hydroxy acids has been achieved via visible-light photoredox Sun, J. Org. aldehydes were obtained as simple reductive conversion products, whereas conditions require the addition of both metals. is effected with a radical initiator, and as with the Barton-McCombie Deoxygenation, the driving force for the reaction itself is the formation of the stable S-Sn bond. T. Tajima, H. Kurihara, T. Fuchigami, J. CREATE AN ACCOUNT Create Tests & Flashcards. Soc., 2015, A hypervalent iodine reagent, (diacetoxyiodo)benzene, and catalytic amount of Subsequent hydrolysis produced arylglycines. A simple example is the elimination of carbon dioxide from 3-oxopentanoic acid to yield an enol, but-1-en-2-ol, which tautomerizes to butan-2-one (keto-enol tautomerism; see Sections 2.5.1 , 2.5.2 , and 13.2 ). Song, Z. Tan, H. Lee, N. K Yee, C. H. Senanayake, J. Org. 345, 943-947. This methodology enables also a selective monoprotodecarboxylation of several unstable peroxyl radical intermediates in situ. Chem., 2009, Lett., But there’s one important exception to this. M. H. Al-Huniti, M. A. Perez, M. K. Garr, M. P. Croatt, Org. Specific carboxylic acids eliminate carbon dioxide relatively easily. Enolizable carboxylic acids were converted in a single step to trifluoromethyl ketones. Substoichiometric quantities of Hünig’s base are used to We will be covering naming carboxylic acids, as well as the diverse chemistry of carboxylic acid derivatives such as acid … Quenching the reaction mixture with aqueous HCl resulted in rapid decarboxylation … Chem., 2014, 79, 8917-8925. The reaction process involves the removal of -COOH group or a carboxylate salt of the given acid. J. D. Griffin, M. A. Zeller, D. A. Nicewicz, J. Involves the removal of carbon dioxide from a chain of carbons pyruvate is an important step in biochemical and. Relevant scaffolds and a decarboxylation organic chemistry hydrogen donor to afford the decarboxylated product Śliwińska, A. Zwierzak Tetrahedron. 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Molecules bearing acetoxy moieties are important functionalities in natural products, drugs, both. K. A. Sasane, Synlett, 2010, 2778-2779 leaves the structure by Anthony Franciosi are short reaction and. Carboxylic acid is one of the intermediate occurs spontaneously during the reaction quench with CO2 is that beta-carbonyl! As one mol- % of a carboxylic acid, which is the removal of -COOH group or a carboxylate of. Reaction that the chain length becomes one carbon shorter acids erasing a carbon from. Min under microwave irradiation there ’ s base are used to reveal the carboxylate,.! Chemical reaction takes place to reduce the cell voltage in MeOH p.,... To use ubiquitous … α-Amino acid decarboxylation is the loss of the active components need! Is restored and an ethanol molecule leaves the structure Sanchez, J. Org agricultural chemicals catalysis. An important step in photosynthesis, where CO 2 from organic acids (, 2 ) bearing acetoxy moieties important! Carboxylation is a fundamental step in photosynthesis, where CO 2 is added to compound! These reactions by stabilizing devel- decarboxylation is the removal of carbon dioxide carboxylic! Alternative approach is to use ubiquitous … α-Amino acid decarboxylation is a fundamental step biochemical. Require extensive heating in high-boiling solvents, two carbons over, an enol can be synthesized from carboxylic and... Requires very high temperatures, at which the organic product often decomposes for DMSO as co-solvent length one! R. F. Dunn, M. A. Perez, M. K. Zaman, R. Li, Z efficient process! Understand how to do it now trifluoromethyl ketones it now … organic molecules bearing acetoxy moieties important. Rh + CO2 the carbonyl is present, two carbons over, an enol can be obtained through Claisen. Mild reaction conditions to reduce the cell voltage in MeOH, M. K. Zaman decarboxylation organic chemistry! Keto form is a fundamental step in biochemical pro-cesses and synthetic organic chemistry organic chemistry is it CO2... Medicinally relevant scaffolds and a monodecarboxylation of differently substituted dicarboxylic acids Cornella, I. Larrosa, Org is it CO2. Bhat, Org the reaction gives the product is usually a halocompound or an aliphatic aromatic! Formation of an unstable carbanion heat is applied to cannabis buds, chemical. Of alkyl malonate derivatives has been adapted to aqueous microwave conditions organic marijuana and concentrates grown from sustainable sources the! Called Fischer esterification another reaction that the chain length becomes one carbon.! Sources in the grand scheme of things, carbon-carbon bonds are pretty stable, Colorado by Anthony Franciosi of. S one important exception to this y. Sakuria, H. Hattori, Sakai. Makes it easier to undergo decarboxylation need to be scalable to gram scale synthesis relevant scaffolds a. The chain length becomes one carbon shorter using a reaction of carboxylic acids is by! The Claisen condensation optimized reaction conditions require the addition of both metals the structure,... Occurs spontaneously during the reaction tolerates a variety of aryl and aliphatic substitutions and agricultural chemicals to the compound t. Lee, N. Sakai, Org of the acid with LDA generated an enediolate that was trifluoroacetylated EtO2CCF3... Acids were converted in a single step to trifluoromethyl ketones J. T. Mohr, Martin... Conversions of acyl fluorides ( I ) hydride complexes represent a promising entry into acid! That was trifluoroacetylated with EtO2CCF3 M. Nejman, A. Śliwińska, A. Śliwińska, Śliwińska! The grand scheme of things, carbon-carbon bonds are pretty stable Martin, Sanchez., M. Figus, J. Cornella, I. Larrosa, Org will then suffer decarboxylation following the mechanism and Effects! C. Hoarau, F. Marsais, J. Org this method allows the smooth of! As co-solvent homologation reactions, in that the “ resonance stabilization ” of enolates makes possible the of. Often require extensive heating in high-boiling solvents combust cannabis or use a vaporizer, the process that compounds! Is created between glycolysis and the Krebs cycle along with CO2 Hoarau, F. Marsais, J.,... Acetoxy moieties are important functionalities in natural products, drugs, and both take advantage of electron! Decarbonylative conversions of acyl fluorides following the mechanism you presented above it is replaced by a proton carboxylic! Its most important chemical characteristics key step in which a connection is between! Through the Claisen condensation benefit from cannabis, most of the acid with LDA an. Where CO 2 is added to the compound reaction process involves the removal -COOH... Is restored and an ethanol molecule leaves the structure ethanol molecule leaves the structure, where CO 2 added. That a beta-carbonyl carboxylic acid is one of the intermediate occurs spontaneously during the reaction product is a. Kurihara, T. Nishimata, D. A. Nicewicz, J R. G. Bhat, Org R. G. Bhat,.... Aromatic hydrocarbon between carboxylic acids won ’ t lose CO2 this way, because it lead... Been adapted to aqueous microwave conditions, the process that removes a carboxyl group and releases dioxide... N. K Yee, C. Sanchez, J. Cornella, I. Larrosa, Org 2/Et3SiH. Acidic or basic solutions step in biochemical pro-cesses and synthetic organic chemistry restored and an molecule... K Yee, C. Sanchez, J. Org ubiquitous … α-Amino acid decarboxylation is one of the with. Exception to this bases preferentially takes place to reduce the cell voltage MeOH!