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

ABSTRACT: 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.

SUBMITTER: Wu S

PROVIDER: S-EPMC5645731 | biostudies-literature | 2015 Apr

REPOSITORIES: biostudies-literature

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

Wu Shangze S Zeng Rong R Fu Chunling C Yu Yihua Y Zhang Xue X Ma Shengming S

Chemical science 20150205 4

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. ...[more]

PMID: 29308141

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