4.8 Article

Decarbonylative Suzuki-Miyaura Cross-Coupling of Aroyl Chlorides

Journal

ORGANIC LETTERS
Volume 22, Issue 16, Pages 6434-6440

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c02250

Keywords

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Funding

  1. NSF [CAREER CHE-1650766]
  2. NIH [1R35GM133326]
  3. Rutgers University
  4. NSFC [21702182, 21873081]
  5. Fundamental Research Funds for the Central Universities
  6. Zhejiang University

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Herein, we report a catalyst system for Pd-catalyzed decarbonylative Suzuki-Miyaura cross-coupling of aroyl chlorides with boronic acids to furnish biaryls. This strategy is suitable for a broad range of common aroyl chlorides and boronic acids. The synthetic utility is highlighted in the direct late-stage functionalization of pharmaceuticals and natural products capitalizing on the presence of carboxylic acid moiety. Extensive mechanistic and DFT studies provide key insight into the reaction mechanism and high decarbonylative cross-coupling selectivity.

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