期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 61, 期 32, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202205656
关键词
Glycosides; Site Selectivity; meta Functionalization; C-H Activation; Ruthenium
资金
- National Natural Science Foundation of China [22171114, 22101232, 21871115]
This paper describes a new ruthenium-catalyzed method for the ortho- and meta-C-Ar-H glycosylation, resulting in the synthesis of various C-aryl pyranosides and furanosides. The method shows broad substrate scope and compatibility with different N-heterocyclic directing groups. Mechanistic studies suggest different pathways for ortho- and meta-C-Ar-H glycosylation, and density functional theory calculations provide an explanation for the high stereoselectivity observed in the meta-C-Ar-H glycosylation.
C-aryl glycosides are popular basic skeletons in biochemistry and pharmaceutical chemistry. Herein, ruthenium-catalyzed highly stereo- and site-selective ortho- and meta-C-Ar-H glycosylation is described. A series of C-aryl pyranosides and furanosides were synthesized by this method. The strategy showed good substrate scope, and various N-heterocyclic directing groups were compatible with the reaction system. A mechanistic study suggested that the key pathway of ortho-C-Ar-H glycosylation might involve oxidative addition/reduction elimination, whereas aryl meta-C-H glycosylation was mediated by sigma-activation. Density functional theory calculations also showed that the high stereoselectivity of meta-C-Ar-H glycosylation was due to steric hindrance.
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