Literature DB >> 31877036

Direct Decarboxylative Functionalization of Carboxylic Acids via O-H Hydrogen Atom Transfer.

Christina G Na1, Davide Ravelli2, Erik J Alexanian1.   

Abstract

Decarboxylative functionalization via hydrogen atom transfer offers an attractive alternative to standard redox approaches to this important class of transformations. Herein, we report a direct decarboxylative functionalization of aliphatic carboxylic acids using N-xanthylamides. The unique reactivity of amidyl radicals in hydrogen atom transfer enables decarboxylative xanthylation under redox-neutral conditions. This platform provides expedient access to a range of derivatives through subsequent elaboration of the xanthate group.

Entities:  

Year:  2019        PMID: 31877036      PMCID: PMC7147874          DOI: 10.1021/jacs.9b10825

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  39 in total

1.  Powerful carbon-carbon bond forming reactions based on a novel radical exchange process.

Authors:  Béatrice Quiclet-Sire; Samir Z Zard
Journal:  Chemistry       Date:  2006-08-07       Impact factor: 5.236

2.  Photoinduced decarboxylative borylation of carboxylic acids.

Authors:  Alexander Fawcett; Johan Pradeilles; Yahui Wang; Tatsuya Mutsuga; Eddie L Myers; Varinder K Aggarwal
Journal:  Science       Date:  2017-06-15       Impact factor: 47.728

3.  Photocatalytic decarboxylative alkylations mediated by triphenylphosphine and sodium iodide.

Authors:  Ming-Chen Fu; Rui Shang; Bin Zhao; Bing Wang; Yao Fu
Journal:  Science       Date:  2019-03-29       Impact factor: 47.728

4.  C-H Xanthylation: A Synthetic Platform for Alkane Functionalization.

Authors:  William L Czaplyski; Christina G Na; Erik J Alexanian
Journal:  J Am Chem Soc       Date:  2016-10-14       Impact factor: 15.419

5.  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

6.  Identifying Amidyl Radicals for Intermolecular C-H Functionalizations.

Authors:  Matthew M Tierney; Stefano Crespi; Davide Ravelli; Erik J Alexanian
Journal:  J Org Chem       Date:  2019-09-06       Impact factor: 4.354

7.  Dual catalysis. Merging photoredox with nickel catalysis: coupling of α-carboxyl sp³-carbons with aryl halides.

Authors:  Zhiwei Zuo; Derek T Ahneman; Lingling Chu; Jack A Terrett; Abigail G Doyle; David W C MacMillan
Journal:  Science       Date:  2014-06-05       Impact factor: 47.728

8.  Silver-Catalyzed Decarboxylative Radical Azidation of Aliphatic Carboxylic Acids in Aqueous Solution.

Authors:  Chao Liu; Xiaoqing Wang; Zhaodong Li; Lei Cui; Chaozhong Li
Journal:  J Am Chem Soc       Date:  2015-07-30       Impact factor: 15.419

9.  Decarboxylative alkenylation.

Authors:  Jacob T Edwards; Rohan R Merchant; Kyle S McClymont; Kyle W Knouse; Tian Qin; Lara R Malins; Benjamin Vokits; Scott A Shaw; Deng-Hui Bao; Fu-Liang Wei; Ting Zhou; Martin D Eastgate; Phil S Baran
Journal:  Nature       Date:  2017-04-19       Impact factor: 49.962

10.  Decarboxylative sp3 C-N coupling via dual copper and photoredox catalysis.

Authors:  Yufan Liang; Xiaheng Zhang; David W C MacMillan
Journal:  Nature       Date:  2018-06-20       Impact factor: 49.962

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  1 in total

1.  Photocatalytic decarboxylative amidosulfonation enables direct transformation of carboxylic acids to sulfonamides.

Authors:  Vu T Nguyen; Graham C Haug; Viet D Nguyen; Ngan T H Vuong; Hadi D Arman; Oleg V Larionov
Journal:  Chem Sci       Date:  2021-04-13       Impact factor: 9.825

  1 in total

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