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Article Dans Une Revue ACS Catalysis Année : 2021

syn-Selective Construction of Fused Heterocycles by Catalytic Reductive Tandem Functionalization of N-Heteroarenes

Résumé

To date, numerous methods have been successfully developed to functionalize N-heteroaryl C-H bonds. In contrast, dearomative tandem functionalization of N-heteroarenes is still a subject to be explored. Reported herein is an example on reductive dearomatization-induced tandem functionalization of N-heteroarenes by ruthenium catalysis, which offers a general method for diastereoselective construction of fused heterocycles featuring a cyclic syn-N, O-acetal motif from N-heteroarenes, phenols, and paraformaldehyde. Mechanistic study reveals that the products are formed via a tandem sequence of pyridyl C-3-benzylation and hydroxymethylation followed by C-2-aryloxylation of N-heteroarenium salts, proceeding with broad substrate scope, good functional group tolerance, high atom efficiency, and applicability for postfunctionalization of some biomedical molecules.
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hal-03331245 , version 1 (01-09-2021)

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Jian Yang, He Zhao, Zhenda Tan, Liang Cao, Huanfeng Jiang, et al.. syn-Selective Construction of Fused Heterocycles by Catalytic Reductive Tandem Functionalization of N-Heteroarenes. ACS Catalysis, 2021, 11 (15), pp.9271-9278. ⟨10.1021/acscatal.1c01328⟩. ⟨hal-03331245⟩
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