4.8 Article

Rhodium-catalyzed C-H functionalization-based approach to eight-membered lactams

Journal

CHEMICAL SCIENCE
Volume 6, Issue 4, Pages 2275-2285

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c5sc00092k

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Funding

  1. National Basic Research Program of China [2015CB856600]
  2. National Natural Science Foundation [21232006, 21472224]

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A Rh(III) catalyzed formal [4 + 2 + 2] cyclization of N-pivaloyloxybenzamides 1 with 1,6-allene-enes 2 by C-H functionalization is reported. The reactions occur at room temperature and are compatible with air and moisture with a tolerance of many synthetically useful functional groups. The follow-up modifications of the products have been demonstrated. After careful mechanistic studies and DFT calculation, a reaction mechanism was proposed.

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