Literature DB >> 26212356

Room-temperature decarboxylative alkynylation of carboxylic acids using photoredox catalysis and EBX reagents.

Franck Le Vaillant1, Thibaut Courant1,2, Jerome Waser3.   

Abstract

Alkynes are used as building blocks in synthetic and medicinal chemistry, chemical biology, and materials science. Therefore, efficient methods for their synthesis are the subject of intensive research. Herein, we report the direct synthesis of alkynes from readily available carboxylic acids at room temperature under visible-light irradiation. The combination of an iridium photocatalyst with ethynylbenziodoxolone (EBX) reagents allowed the decarboxylative alkynylation of carboxylic acids in good yields under mild conditions. The method could be applied to silyl-, aryl-, and alkyl- substituted alkynes. It was particularly successful in the case of α-amino and α-oxo acids derived from biomass.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkynes; amino acids; carboxylic acids; hypervalent iodine; photocatalysis

Year:  2015        PMID: 26212356     DOI: 10.1002/anie.201505111

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  23 in total

1.  Decarboxylative Alkynylation.

Authors:  Joel M Smith; Tian Qin; Rohan R Merchant; Jacob T Edwards; Lara R Malins; Zhiqing Liu; Guanda Che; Zichao Shen; Scott A Shaw; Martin D Eastgate; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-01       Impact factor: 15.336

2.  Light-Driven Intermolecular Charge Transfer Induced Reactivity of Ethynylbenziodoxol(on)e and Phenols.

Authors:  Bin Liu; Chern-Hooi Lim; Garret M Miyake
Journal:  J Am Chem Soc       Date:  2018-10-02       Impact factor: 15.419

3.  Reductive Decarboxylative Alkynylation of N-Hydroxyphthalimide Esters with Bromoalkynes.

Authors:  Liangbin Huang; Astrid M Olivares; Daniel J Weix
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-17       Impact factor: 15.336

4.  Palladium-Catalyzed Enantioselective Redox-Relay Heck Alkynylation of Alkenols To Access Propargylic Stereocenters.

Authors:  Zhi-Min Chen; Christine S Nervig; Ryan J DeLuca; Matthew S Sigman
Journal:  Angew Chem Int Ed Engl       Date:  2017-05-03       Impact factor: 15.336

5.  Photoinduced inverse Sonogashira coupling reaction.

Authors:  Lizhu Zhang; Cunbo Wei; Jiawen Wu; Dan Liu; Yinchao Yao; Zhuo Chen; Jianxun Liu; Chang-Jiang Yao; Dinghua Li; Rongjie Yang; Zhonghua Xia
Journal:  Chem Sci       Date:  2022-05-30       Impact factor: 9.969

6.  Unconventional Reactivity of Ethynylbenziodoxolone Reagents and Thiols: Scope and Mechanism.

Authors:  Bin Liu; Juan V Alegre-Requena; Robert S Paton; Garret M Miyake
Journal:  Chemistry       Date:  2020-01-22       Impact factor: 5.236

Review 7.  Hypervalent Iodine-Mediated Late-Stage Peptide and Protein Functionalization.

Authors:  Emmanuelle M D Allouche; Elija Grinhagena; Jerome Waser
Journal:  Angew Chem Int Ed Engl       Date:  2021-12-08       Impact factor: 16.823

8.  Photoredox Catalysis in Organic Chemistry.

Authors:  Megan H Shaw; Jack Twilton; David W C MacMillan
Journal:  J Org Chem       Date:  2016-08-01       Impact factor: 4.354

9.  Iodine(III) Reagents in Radical Chemistry.

Authors:  Xi Wang; Armido Studer
Journal:  Acc Chem Res       Date:  2017-06-21       Impact factor: 22.384

10.  Photocatalytic Umpolung of N- and O-substituted alkenes for the synthesis of 1,2-amino alcohols and diols.

Authors:  Stephanie G E Amos; Stefano Nicolai; Jerome Waser
Journal:  Chem Sci       Date:  2020-09-22       Impact factor: 9.825

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