Literature DB >> 32941044

Electrochemical Decarboxylative N-Alkylation of Heterocycles.

Tao Sheng1, Hai-Jun Zhang1, Ming Shang1, Chi He1, Julien C Vantourout1, Phil S Baran1.   

Abstract

An operationally simple method to employ nonactivated carboxylic acids as alkylating agents in the N-alkylation of heterocycles is reported through an electrochemically driven anodic decarboxylative process. A wide substrate scope across a range of heterocycles is demonstrated along with a series of applications that significantly reduce the step count required to access such medicinally relevant structures.

Entities:  

Year:  2020        PMID： 32941044      PMCID： PMC8350983          DOI： 10.1021/acs.orglett.0c02799

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  28 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.  Decarboxylative borylation.

Authors:  Chao Li; Jie Wang; Lisa M Barton; Shan Yu; Maoqun Tian; David S Peters; Manoj Kumar; Antony W Yu; Kristen A Johnson; Arnab K Chatterjee; Ming Yan; Phil S Baran
Journal:  Science       Date:  2017-04-13       Impact factor: 47.728

3.  A General Amino Acid Synthesis Enabled by Innate Radical Cross-Coupling.

Authors:  Shengyang Ni; Alberto F Garrido-Castro; Rohan R Merchant; Justine N de Gruyter; Daniel C Schmitt; James J Mousseau; Gary M Gallego; Shouliang Yang; Michael R Collins; Jennifer X Qiao; Kap-Sun Yeung; David R Langley; Michael A Poss; Paul M Scola; Tian Qin; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2018-10-15       Impact factor: 15.336

Review 4.  Transition metal-catalyzed decarboxylative allylation and benzylation reactions.

Authors:  Jimmie D Weaver; Antonio Recio; Alexander J Grenning; Jon A Tunge
Journal:  Chem Rev       Date:  2011-01-14       Impact factor: 60.622

5.  Direct Catalytic Decarboxylative Amination of Aryl Acetic Acids.

Authors:  Duanyang Kong; Patrick J Moon; Odey Bsharat; Rylan J Lundgren
Journal:  Angew Chem Int Ed Engl       Date:  2019-12-05       Impact factor: 15.336

6.  Decarboxylative Csp3-N Bond Formation by Electrochemical Oxidation of Amino Acids.

Authors:  Xiaoqing Shao; Yue Zheng; Lifang Tian; Inmaculada Martín-Torres; Antonio M Echavarren; Yahui Wang
Journal:  Org Lett       Date:  2019-10-29       Impact factor: 6.005

7.  Decarboxylative coupling reactions: a modern strategy for C-C-bond formation.

Authors:  Nuria Rodríguez; Lukas J Goossen
Journal:  Chem Soc Rev       Date:  2011-07-27       Impact factor: 54.564

8.  Cross-Coupling of Alkyl Redox-Active Esters with Benzophenone Imines: Tandem Photoredox and Copper Catalysis.

Authors:  Runze Mao; Jonathan Balon; Xile Hu
Journal:  Angew Chem Int Ed Engl       Date:  2018-06-28       Impact factor: 15.336

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.  Decarboxylative Cross-Coupling: A Radical Tool in Medicinal Chemistry.

Authors:  Gabriele Laudadio; Maximilian D Palkowitz; Tamara El-Hayek Ewing; Phil S Baran
Journal:  ACS Med Chem Lett       Date:  2022-08-10       Impact factor: 4.632
  1 in total

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