Literature DB >> 23724964

Rh[III]-catalyzed C-H amidation using aroyloxycarbamates to give N-Boc protected arylamines.

Christoph Grohmann1, Honggen Wang, Frank Glorius.   

Abstract

The Rh(III)-catalyzed amidation of C(sp(2))-H bonds by the use of electron-deficient aroyloxycarbamates as efficient electrophilic amidation partners is reported. The reaction proceeded under mild conditions with broad functional group tolerance, and pyridine and O-methyl hydroxamic acids serve as efficient directing groups, giving access to valuable N-Boc protected arylamines (also Fmoc and Cbz). Preliminary mechanistic experiments are discussed.

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Year:  2013        PMID: 23724964     DOI: 10.1021/ol401209f

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


  11 in total

1.  Site-Selective Copper-Catalyzed Amination and Azidation of Arenes and Heteroarenes via Deprotonative Zincation.

Authors:  Charles E Hendrick; Katie J Bitting; Seoyoung Cho; Qiu Wang
Journal:  J Am Chem Soc       Date:  2017-08-14       Impact factor: 15.419

Review 2.  C-H bond activation and sequential addition to two different coupling partners: a versatile approach to molecular complexity.

Authors:  Daniel S Brandes; Jonathan A Ellman
Journal:  Chem Soc Rev       Date:  2022-08-01       Impact factor: 60.615

3.  Pd(II)-catalyzed C-H functionalizations directed by distal weakly coordinating functional groups.

Authors:  Gang Li; Li Wan; Guofu Zhang; Dasheng Leow; Jillian Spangler; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2015-03-24       Impact factor: 15.419

4.  Recent Advances in the C-H-Functionalization of the Distal Positions in Pyridines and Quinolines.

Authors:  David E Stephens; Oleg V Larionov
Journal:  Tetrahedron       Date:  2015-08-19       Impact factor: 2.457

5.  Rh(III)-Catalyzed Imidoyl C-H Carbamylation and Cyclization to Bicyclic [1,3,5]Triazinones.

Authors:  Danielle N Confair; Nathaniel S Greenwood; Brandon Q Mercado; Jonathan A Ellman
Journal:  Org Lett       Date:  2020-11-10       Impact factor: 6.005

6.  Copper-catalyzed electrophilic amination of heteroarenes and arenes by C-H zincation.

Authors:  Stacey L McDonald; Charles E Hendrick; Qiu Wang
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-25       Impact factor: 15.336

7.  Rh(iii)-catalyzed tandem annulative redox-neutral arylation/amidation of aromatic tethered alkenes.

Authors:  Chao Chen; Chen Shi; Yaxi Yang; Bing Zhou
Journal:  Chem Sci       Date:  2020-10-16       Impact factor: 9.825

8.  Cu-catalyzed direct amidation of aromatic C-H bonds: an access to arylamines.

Authors:  Hui Xu; Xixue Qiao; Shiping Yang; Zengming Shen
Journal:  J Org Chem       Date:  2014-04-30       Impact factor: 4.354

9.  Copper-catalyzed diamination of unactivated alkenes with hydroxylamines.

Authors:  Kun Shen; Qiu Wang
Journal:  Chem Sci       Date:  2015-05-18       Impact factor: 9.825

10.  Directing group assisted meta-hydroxylation by C-H activation.

Authors:  Arun Maji; Bangaru Bhaskararao; Santanu Singha; Raghavan B Sunoj; Debabrata Maiti
Journal:  Chem Sci       Date:  2016-01-21       Impact factor: 9.825

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