4.8 Article

Highly Selective and Divergent Acyl and Aryl Cross-Couplings of Amides via Ir-Catalyzed C-H Borylation/N-C(O) Activation

Journal

ORGANIC LETTERS
Volume 22, Issue 15, Pages 6010-6015

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c02105

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Funding

  1. Rutgers University
  2. NSF [CAREER CHE-1650766]
  3. NSF-MRI grant [CHE-1229030]
  4. China Scholarship Council [201606240022]

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Herein, we demonstrate that amides can be readily coupled with nonactivated arenes via sequential Ir-catalyzed C-H borylation/N-C(O) activation. This methodology provides facile access to biaryl ketones and biaryls by the sterically controlled Ir-catalyzed C-H borylation and divergent acyl and decarbonylative amide N-C(O) and C-C activation. The methodology diverts the traditional acylation and arylation regioselectivity, allowing us to directly utilize readily available arenes and amides to produce valuable ketone and biaryl motifs.

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