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

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-...

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Published inACS catalysis Vol. 11; no. 15; pp. 9271 - 9278
Main Authors Yang, Jian, Zhao, He, Tan, Zhenda, Cao, Liang, Jiang, Huanfeng, Ci, Chenggang, Dixneuf, Pierre H, Zhang, Min
Format Journal Article
LanguageEnglish
Published American Chemical Society 06.08.2021
Subjects
Chemical Sciences
diastereoselectivity
ruthenium catalysis
tandem functionalization
N-heteroarenes
reductive dearomatization
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Summary: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 C3-benzylation and hydroxymethylation followed by C2-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.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.1c01328