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Pure Appl. Chem., 2008, Vol. 80, No. 8, pp. 1725-1733

http://dx.doi.org/10.1351/pac200880081725

New catalytic transformations of carboxylic acids

Lukas J. Gooßen, Käthe Gooßen, Nuria Rodríguez, Mathieu Blanchot, Christophe Linder and Bettina Zimmermann

FB Chemie - Department of Organic Chemistry, Technical University Kaiserslautern, Erwin-Schrödinger-Str. Geb. 54, 67663 Kaiserslautern, Germany

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  • Rijs Nicole J., Yoshikai Naohiko, Nakamura Eiichi, O’Hair Richard A. J.: Unraveling Organocuprate Complexity: Fundamental Insights into Intrinsic Group Transfer Selectivity in Alkylation Reactions. J. Org. Chem. 2014, 79, 1320. <http://dx.doi.org/10.1021/jo4027325>
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  • Iwasaki Takanori, Higashikawa Kiyokazu, Reddy Vutukuri P., Ho Willbe W. S., Fujimoto Yukari, Fukase Koichi, Terao Jun, Kuniyasu Hitoshi, Kambe Nobuaki: NickelButadiene Catalytic System for the Cross-Coupling of Bromoalkanoic Acids with Alkyl Grignard Reagents: A Practical and Versatile Method for Preparing Fatty Acids. Chem. Eur. J. 2013, 19, 2956. <http://dx.doi.org/10.1002/chem.201204222>
  • Wei Siping, Pedroni Julia, Meißner Antje, Lumbroso Alexandre, Drexler Hans-Joachim, Heller Detlef, Breit Bernhard: Development of an Improved Rhodium Catalyst for Z -Selective Anti-Markovnikov Addition of Carboxylic Acids to Terminal Alkynes. Chem. Eur. J. 2013, 19, 12067. <http://dx.doi.org/10.1002/chem.201300160>
  • Bhowmik Subhendu, Pandey Garima, Batra Sanjay: Substituent-Guided Switch between CH Activation and Decarboxylative Cross-Coupling during Palladium/Copper-Catalyzed Cascade Reactions of 2-Aminobenzoates with 2-Haloarylaldehydes. Chem. Eur. J. 2013, 19, 10487. <http://dx.doi.org/10.1002/chem.201301705>
  • Patra Tuhin, Deb Arghya, Manna Srimanta, Sharma Upendra, Maiti Debabrata: Iron-Mediated Decarboxylative Trifluoromethylation of α,β-Unsaturated Carboxylic Acids with Trifluoromethanesulfinate. Eur. J. Org. Chem. 2013, 2013, 5247. <http://dx.doi.org/10.1002/ejoc.201300473>
  • Grünberg Matthias F., Gooßen Lukas J.: Decarboxylative allylation of arylglyoxylic acids with allyl alcohol. Journal of Organometallic Chemistry 2013, 744, 140. <http://dx.doi.org/10.1016/j.jorganchem.2013.06.004>
  • Jafarpour Farnaz, Zarei Samaneh, Barzegar Amiri Olia Mina, Jalalimanesh Nafiseh, Rahiminejadan Soraya: Palladium-Catalyzed Decarboxylative Cross-Coupling Reactions: A Route for Regioselective Functionalization of Coumarins. J. Org. Chem. 2013, 78, 2957. <http://dx.doi.org/10.1021/jo302778d>
  • Wang Lei, Ren Xinyi, Yu Jintao, Jiang Yan, Cheng Jiang: Base-Promoted Formal Arylation of Benzo[d]oxazoles with Acyl Chloride. J. Org. Chem. 2013, 78, 12076. <http://dx.doi.org/10.1021/jo402106q>
  • Li Zejiang, Cui Zili, Liu Zhong-Quan: Copper- and Iron-Catalyzed Decarboxylative Tri- and Difluoromethylation of α,β-Unsaturated Carboxylic Acids with CF3SO2Na and (CF2HSO2)2Zn via a Radical Process. Org. Lett. 2013, 15, 406. <http://dx.doi.org/10.1021/ol3034059>
  • Miao Jinmin, Ge Haibo: Palladium-Catalyzed Chemoselective Decarboxylative Ortho Acylation of Benzoic Acids with α-Oxocarboxylic Acids. Org. Lett. 2013, 15, 2930. <http://dx.doi.org/10.1021/ol400919u>
  • Pandey Garima, Bhowmik Subhendu, Batra Sanjay: Synthesis of 3H-Pyrazolo[3,4-c]isoquinolines and Thieno[3,2-c]isoquinolines via Cascade Imination/Intramolecular Decarboxylative Coupling. Org. Lett. 2013, 15, 5044. <http://dx.doi.org/10.1021/ol4023722>
  • Khairallah George N., Thum Charlene C. L., Lesage Denis, Tabet Jean-Claude, O’Hair Richard A. J.: Gas-Phase Formation and Fragmentation Reactions of the Organomagnesates [RMgX2]−. Organometallics 2013, 32, 2319. <http://dx.doi.org/10.1021/om3011917>
  • Woolley Matthew J., Khairallah George N., da Silva Gabriel, Donnelly Paul S., Yates Brian F., O’Hair Richard A. J.: Role of the Metal, Ligand, and Alkyl/Aryl Group in the Hydrolysis Reactions of Group 10 Organometallic Cations [(L)M(R)]+. Organometallics 2013, 32, 6931. <http://dx.doi.org/10.1021/om400358q>
  • Al Sharif Halah, Vikse Krista L., Khairallah George N., O’Hair Richard A. J.: Catalytic Decarboxylative Coupling of Allyl Acetate: Role of the Metal Centers in the Organometallic Cluster Cations [CH3Cu2]+, [CH3AgCu]+, and [CH3Ag2]+. Organometallics 2013, 32, 5416. <http://dx.doi.org/10.1021/om400712n>
  • Yu Lin, Li Pinhua, Wang Lei: Copper-promoted decarboxylative direct C3-acylation of N-substituted indoles with α-oxocarboxylic acids. Chem. Commun. 2013, 49, 2368. <http://dx.doi.org/10.1039/c3cc40389k>
  • Vikse Krista, Khairallah George N., McIndoe J. Scott, O'Hair Richard A. J.: Fixed-charge phosphine ligands to explore gas-phase coinage metal-mediated decarboxylation reactions. Dalton Trans. 2013, 42, 6440. <http://dx.doi.org/10.1039/c3dt32285h>
  • Khan Bilal A., Buba Annette E., Gooßen Lukas J.: Oxidative Trifluoromethylation of Arylboronates with Shelf-Stable Potassium (Trifluoromethyl)trimethoxyborate. Chemistry A European Journal 2012, 18, 1577. <http://dx.doi.org/10.1002/chem.201102652>
  • Tartaggia Stefano, De Lucchi Ottorino, Gooßen Lukas J.: Practical Synthesis of Unsymmetrical Diarylacetylenes from Propiolic Acid and Two Different Aryl Bromides. Eur J Org 2012, 2012, 1431. <http://dx.doi.org/10.1002/ejoc.201101770>
  • Miki Yasuyoshi, Umemoto Hideaki, Dohshita Masashi, Hamamoto Hiromi: Synthesis of pyrrolophenanthridone alkaloid kalbretorine from indolecarboxylic acids via hypervalent iodine(III) mediated halodecarboxylation and reduction. Tetrahetron Lett 2012, 53, 1924. <http://dx.doi.org/10.1016/j.tetlet.2012.01.132>
  • Rudolphi Felix, Goossen Lukas J.: Electronic Laboratory Notebook: The Academic Point of View. J  Chem Inf Model 2012, 52, 293. <http://dx.doi.org/10.1021/ci2003895>
  • Rijs Nicole J., Yoshikai Naohiko, Nakamura Eiichi, O’Hair Richard A. J.: Gas-Phase Reactivity of Group 11 Dimethylmetallates with Allyl Iodide. S J Am Chem Soc 2012, 134, 2569. <http://dx.doi.org/10.1021/ja2069032>
  • Mamone Patrizia, Grünberg Matthias F., Fromm Andreas, Khan Bilal A., Gooßen Lukas J.: [Pd(μ-Br)(PtBu3)]2 as a Highly Active Isomerization Catalyst: Synthesis of Enol Esters from Allylic Esters. Org. Lett. 2012, 14, 3716. <http://dx.doi.org/10.1021/ol301563g>
  • Sraj Lenka O’Connor, Khairallah George N., da Silva Gabriel, O’Hair Richard A. J.: Who Wins: Pesci, Peters, or Deacon? Intrinsic Reactivity Orders for Organocuprate Formation via Ligand Decomposition. Organomettalics 2012, 31, 1801. <http://dx.doi.org/10.1021/om2011722>
  • Rijs Nicole J., O'Hair Richard A. J.: Forming trifluoromethylmetallates: competition between decarboxylation and C–F bond activation of group 11 trifluoroacetate complexes, [CF3CO2ML]−. DALTON T 2012, 41, 3395. <http://dx.doi.org/10.1039/c2dt12117d>
  • Dzik Wojciech I., Lange Paul P., Gooßen Lukas J.: Carboxylates as sources of carbon nucleophiles and electrophiles: comparison of decarboxylative and decarbonylative pathways. Chem. Sci. 2012, 3, 2671. <http://dx.doi.org/10.1039/c2sc20312j>
  • Cui Zili, Shang Xiaojie, Shao Xiang-Feng, Liu Zhong-Quan: Copper-catalyzed decarboxylative alkenylation of sp3 C–H bonds with cinnamic acids via a radical process. Chem. Sci. 2012, 3, 2853. <http://dx.doi.org/10.1039/c2sc20712e>
  • Li Tingyi, Qu Xiaoming, Zhu Yan, Sun Peng, Yang Hailong, Shan Yuqin, Zhang Hongxin, Liu Defu, Zhang Xiang, Mao Jincheng: Synthesis of Diarylalkynes by Iron/Copper Co-Catalyzed Decarboxylative spsp2 Coupling of Alkynyl Carboxylic Acids and Aryl Halides. Synth Catal 2011, 353, 2731. <http://dx.doi.org/10.1002/adsc.201100238>
  • Boersch Christina, Merkul Eugen, Müller Thomas J. J.: Katalytische Synthesen N-heterocyclischer Inone und Indione durch In-situ-Aktivierung von Carbonsäuren mit Oxalylchlorid. angew chemie 2011, 123, 10632. <http://dx.doi.org/10.1002/ange.201103296>
  • Boersch Christina, Merkul Eugen, Müller Thomas J. J.: Catalytic Syntheses of N-Heterocyclic Ynones and Ynediones by In Situ Activation of Carboxylic Acids with Oxalyl Chloride. Angew. Chem. Int. Ed. 2011, 50, 10448. <http://dx.doi.org/10.1002/anie.201103296>
  • Rodríguez Nuria, Manjolinho Filipe, Grünberg Matthias F., Gooßen Lukas J.: Synthesis of α,β-Unsaturated Ketones by Pd-Catalyzed Decarboxylative Allylation of α-Oxocarboxylates. Chemistry A European Journal 2011, 17, 13688. <http://dx.doi.org/10.1002/chem.201102584>
  • Rossi Renzo, Bellina Fabio, Lessi Marco: Highly selective palladium-catalyzed Suzuki–Miyaura monocoupling reactions of ethene and arene derivatives bearing two or more electrophilic sites. Tetrahed 2011, 67, 6969. <http://dx.doi.org/10.1016/j.tet.2011.06.001>
  • Arndt Matthias, Salih Kifah S. M., Fromm Andreas, Goossen Lukas J., Menges Fabian, Niedner-Schatteburg Gereon: Mechanistic Investigation of the Ru-Catalyzed Hydroamidation of Terminal Alkynes. J Am Chem Soc 2011, 133, 7428. <http://dx.doi.org/10.1021/ja111389r>
  • Leeming Michael G., Khairallah George N., da Silva Gabriel, O’Hair Richard A. J.: Modeling Solvation of Magnesium Centers by Ether Ligands: Gas-Phase Synthesis and Hydrolysis of the Organomagnesium Cations [CH3Mg(3X-crown-X)]+ (X = 4–6). Organomettalics 2011, 30, 4297. <http://dx.doi.org/10.1021/om200359w>
  • Li Huajie, Wu Long-Min, Liu Zhongquan, Wang Jiantao, Cui Zili, Zhang Yuexia: Pd(ii)-catalyzed decarboxylative allylation and Heck-coupling of arene carboxylates with allylic halides and esters. Org Biomol Chem 2011, 9, 663. <http://dx.doi.org/10.1039/c0ob00696c>
  • Li Mingzong, Wang Cong, Fang Ping, Ge Haibo: Pd(ii)-catalyzed decarboxylative cross-coupling of oxamic acids with potassium phenyltrifluoroborates under mild conditions. Chem Commun 2011, 47, 6587. <http://dx.doi.org/10.1039/c1cc11635e>
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  • Bramborg Andrea, Linker Torsten: Selective Synthesis of 1,4-Dialkylbenzenes from Terephthalic Acid. Synth Catal 2010, 352, 2195. <http://dx.doi.org/10.1002/adsc.201000322>
  • Gooßen Lukas J., Rodríguez Nuria, Linder Christophe, Lange Paul P., Fromm Andreas: Comparative Study of Copper- and Silver-Catalyzed Protodecarboxylations of Carboxylic Acids. ChemCatChem 2010, 2, 430. <http://dx.doi.org/10.1002/cctc.200900277>
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  • Bonesi Sergio M., Fagnoni Maurizio: The Aromatic Carbon-Carbon ipso-Substitution Reaction. Chem Eur J 2010, 16, 13572. <http://dx.doi.org/10.1002/chem.201001478>
  • Goossen Lukas J., Collet Florence, Goossen Käthe: Decarboxylative Coupling Reactions. Isr J Chem 2010, 50, 617. <http://dx.doi.org/10.1002/ijch.201000039>
  • Fang Ping, Li Mingzong, Ge Haibo: Room Temperature Palladium-Catalyzed Decarboxylative ortho-Acylation of Acetanilides with α-Oxocarboxylic Acids. J Am Chem Soc 2010, 132, 11898. <http://dx.doi.org/10.1021/ja105245f>
  • Shuai Qi, Yang Luo, Guo Xiangyu, Baslé Olivier, Li Chao-Jun: Rhodium-Catalyzed Oxidative C−H Arylation of 2-Arylpyridine Derivatives via Decarbonylation of Aromatic Aldehydes. J Am Chem Soc 2010, 132, 12212. <http://dx.doi.org/10.1021/ja105396b>
  • Rijs Nicole J., Sanvido Gustavo B., Khairallah George N., O'Hair Richard A. J.: Gas phase synthesis and reactivity of dimethylaurate. Dalton Trans 2010, 39, 8655. <http://dx.doi.org/10.1039/c0dt00508h>
  • Goo��en Lukas���J., Zimmermann Bettina, Linder Christophe, Rodr��guez Nuria, Lange Paul���P., Hartung Jens: Synthesis of Biaryls and Aryl Ketones via Microwave-Assisted Decarboxylative Cross-Couplings. Adv Synth Catal 2009, 351, 2667. <http://dx.doi.org/10.1002/adsc.200900337>
  • Gooßen Lukas J., Linder Christophe, Rodríguez Nuria, Lange Paul P., Fromm Andreas: Silver-catalysed protodecarboxylation of carboxylic acids. Chem Commun 2009, 7173. <http://dx.doi.org/10.1039/b912509d>
  • Goossen Lukas J., Goossen Kaethe, Rodriguez Nuria, Blanchot Mathieu, Linder Christophe, Zimmermann Bettina: ChemInform Abstract: New Catalytic Transformations of Carboxylic Acids. ChemInform 2008, 39. <http://dx.doi.org/10.1002/chin.200850246>