Literature DB >> 16888137

Synthesis of biaryls via catalytic decarboxylative coupling.

Lukas J Goossen1, Guojun Deng, Laura M Levy.   

Abstract

We present a safe and convenient cross-coupling strategy for the large-scale synthesis of biaryls, commercially important structures often found in biologically active molecules. In contrast to traditional cross-couplings, which require the prior preparation of organometallic reagents, we use a copper catalyst to generate the carbon nucleophiles in situ, via decarboxylation of easily accessible arylcarboxylic acid salts. The scope and potential economic impact of the reaction are demonstrated by the synthesis of 26 biaryls, one of which is an intermediate in the large-scale production of the agricultural fungicide Boscalid.

Entities:  

Year:  2006        PMID: 16888137     DOI: 10.1126/science.1128684

Source DB:  PubMed          Journal:  Science        ISSN: 0036-8075            Impact factor:   47.728


  51 in total

1.  Deacylative allylation: allylic alkylation via retro-Claisen activation.

Authors:  Alexander J Grenning; Jon A Tunge
Journal:  J Am Chem Soc       Date:  2011-08-24       Impact factor: 15.419

2.  Methoxy-directed aryl-to-aryl 1,3-rhodium migration.

Authors:  Jing Zhang; Jun-Feng Liu; Angel Ugrinov; Anthony F X Pillai; Zhong-Ming Sun; Pinjing Zhao
Journal:  J Am Chem Soc       Date:  2013-11-07       Impact factor: 15.419

3.  Decarboxylative Coupling Reaction in ESI(-)-MS/MS of 4-Nitrobenzyl 4-Hydroxybenzoates: Triplet Ion-Neutral Complex-Mediated 4-Nitrobenzyl Transfer.

Authors:  Xiaoping Zhang; Xingfeng Bai; Liwen Fang; Kezhi Jiang; Zuguang Li
Journal:  J Am Soc Mass Spectrom       Date:  2016-02-29       Impact factor: 3.109

4.  Hydrodecarboxylation of Carboxylic and Malonic Acid Derivatives via Organic Photoredox Catalysis: Substrate Scope and Mechanistic Insight.

Authors:  Jeremy D Griffin; Mary A Zeller; David A Nicewicz
Journal:  J Am Chem Soc       Date:  2015-08-28       Impact factor: 15.419

5.  Palladium- and Nickel-Catalyzed Decarbonylative C-S Coupling to Convert Thioesters to Thioethers.

Authors:  Naoko Ichiishi; Christian A Malapit; Łukasz Woźniak; Melanie S Sanford
Journal:  Org Lett       Date:  2017-12-07       Impact factor: 6.005

6.  Pd-Catalyzed Decarbonylative Cross-Couplings of Aroyl Chlorides.

Authors:  Christian A Malapit; Naoko Ichiishi; Melanie S Sanford
Journal:  Org Lett       Date:  2017-07-19       Impact factor: 6.005

7.  Palladium-catalyzed decarboxylative sp3-sp3 coupling of nitrobenzene acetic esters.

Authors:  Shelli R Waetzig; Jon A Tunge
Journal:  J Am Chem Soc       Date:  2007-11-08       Impact factor: 15.419

8.  A copper-catalyzed, pH-neutral construction of high-enantiopurity peptidyl ketones from peptidic s-acylthiosalicylamides in air at room temperature.

Authors:  Lanny S Liebeskind; Hao Yang; Hao Li
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

9.  Pd-catalyzed decarboxylative Heck vinylation of 2-nitrobenzoates in the presence of CuF₂.

Authors:  Lukas J Gooßen; Bettina Zimmermann; Thomas Knauber
Journal:  Beilstein J Org Chem       Date:  2010-05-03       Impact factor: 2.883

10.  Structure-activity relationship study of bone morphogenetic protein (BMP) signaling inhibitors.

Authors:  Gregory D Cuny; Paul B Yu; Joydev K Laha; Xuechao Xing; Ji-Feng Liu; Carol S Lai; Donna Y Deng; Chetana Sachidanandan; Kenneth D Bloch; Randall T Peterson
Journal:  Bioorg Med Chem Lett       Date:  2008-06-27       Impact factor: 2.823

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