Literature DB >> 33215815

Functionalization of α-C(sp3 )-H Bonds in Amides Using Radical Translocating Arylating Groups.

Niklas Radhoff1, Armido Studer1.   

Abstract

α-C-H arylation of N-alkylamides using 2-iodoarylsulfonyl radical translocating arylating (RTA) groups is reported. The method allows the construction of α-quaternary carbon centers in amides. Various mono- and disubstituted RTA-groups are applied to the arylation of primary, secondary, and tertiary α-C(sp3 )-H-bonds. These radical transformations proceed in good to excellent yields and the cascades comprise a 1,6-hydrogen atom transfer, followed by a 1,4-aryl migration with subsequent SO2 extrusion.
© 2020 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.

Entities:  

Keywords:  aryl migration; hydrogen atom transfer; radical; visible light catalysis

Year:  2020        PMID: 33215815     DOI: 10.1002/anie.202013275

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


  12 in total

1.  Modular synthesis of α-arylated carboxylic acids, esters and amides via photocatalyzed triple C-F bond cleavage of methyltrifluorides.

Authors:  Sifan Li; Paul W Davies; Wei Shu
Journal:  Chem Sci       Date:  2022-05-12       Impact factor: 9.969

2.  Cobalt-catalyzed chemoselective dehydrogenation through radical translocation under visible light.

Authors:  Wan-Lei Yu; Zi-Gang Ren; Ke-Xing Ma; Hui-Qing Yang; Jun-Jie Yang; Haixue Zheng; Wangsuo Wu; Peng-Fei Xu
Journal:  Chem Sci       Date:  2022-06-15       Impact factor: 9.969

3.  Site-selective coupling of remote C(sp3)-H/meta-C(sp2)-H bonds enabled by Ru/photoredox dual catalysis and mechanistic studies.

Authors:  Hong-Chao Liu; Xiangtao Kong; Xiao-Ping Gong; Yuke Li; Zhi-Jie Niu; Xue-Ya Gou; Xue-Song Li; Yu-Zhao Wang; Wei-Yu Shi; Yan-Chong Huang; Xue-Yuan Liu; Yong-Min Liang
Journal:  Chem Sci       Date:  2022-04-12       Impact factor: 9.969

Review 4.  Aryl Transfer Strategies Mediated by Photoinduced Electron Transfer.

Authors:  Anthony R Allen; Efrey A Noten; Corey R J Stephenson
Journal:  Chem Rev       Date:  2021-10-21       Impact factor: 72.087

5.  Directed Ni-Catalyzed Reductive Arylation of Aliphatic C-H Bonds.

Authors:  Zhi-Yun Liu; Silas P Cook
Journal:  Org Lett       Date:  2022-05-02       Impact factor: 6.072

6.  1,4-Aryl migration in ketene-derived enolates by a polar-radical-crossover cascade.

Authors:  Niklas Radhoff; Armido Studer
Journal:  Nat Commun       Date:  2022-06-02       Impact factor: 17.694

7.  Diarylamine Synthesis via Desulfinylative Smiles Rearrangement.

Authors:  Thomas Sephton; Jonathan M Large; Sam Butterworth; Michael F Greaney
Journal:  Org Lett       Date:  2022-01-30       Impact factor: 6.005

8.  Radical boron migration of allylboronic esters.

Authors:  Xiangzhang Tao; Shengyang Ni; Lingyu Kong; Yi Wang; Yi Pan
Journal:  Chem Sci       Date:  2022-01-17       Impact factor: 9.825

Review 9.  Recent Breakthroughs in P4 Chemistry: Towards Practical, Direct Transformations into P1 Compounds.

Authors:  Daniel J Scott
Journal:  Angew Chem Int Ed Engl       Date:  2022-05-25       Impact factor: 16.823

10.  Selective [2+1+1] Fragmentation of P4 by heteroleptic Metallasilylenes.

Authors:  Juliane Schoening; Alexander Gehlhaar; Christoph Wölper; Stephan Schulz
Journal:  Chemistry       Date:  2022-06-23       Impact factor: 5.020

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