C-N and C-O Bond Formation in Copper-Catalyzed/Mediated sp3C-H Activation: Mechanistic Studies from Experimental and Computational Aspects

Yuhang Yang, Fei Cao, Linbin Yao, Tao Shi, Bencan Tang, Yoichiro Kuninobu, Zhen Wang

研究成果: Contribution to journalArticle査読

1 被引用数 (Scopus)

抄録

Mechanistic studies on Cu-catalyzed/mediated sp3 C-H amidation and acetoxylation are investigated from experimental and computational aspects. The concerted metalation-deprotonation (CMD) mechanism rather than a radical-involved pathway is proved to occur in amidation and acetoxylation reactions, and this is the rare example of the CMD mechanism involved in the more challenging sp3 C-H activations. Theoretical calculations demonstrated that CMD is the rate-determining step either for methylic or benzylic positions in amidation and acetoxylation reactions, and intermolecular nucleophilic addition of acetate anions is more favorable than the ring opening of β-lactams and intramolecular acetoxylation. These mechanistic studies on the divergent and condition-dependent product formation are critical for developing Cu-promoted C-H functionalization via the CMD mechanism.

本文言語英語
ページ(範囲)9713-9726
ページ数14
ジャーナルJournal of Organic Chemistry
85
15
DOI
出版ステータス出版済み - 8 7 2020

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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