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Sonogashira-Hagihara reactions of halogenated glycals.

ABSTRACT: Herein, we report on our findings of the Sonogashira-Hagihara reaction with 1-iodinated and 2-brominated glycals using several aromatic and aliphatic alkynes. This Pd-catalyzed cross-coupling reaction presents a facile access to alkynyl C-glycosides and sets the stage for a reductive/oxidative refunctionalization of the enyne moiety to regenerate either C-glycosidic structures or pyran derivatives with a substituent in position 2.

SUBMITTER: Koester DC

PROVIDER: S-EPMC3388853 | biostudies-literature | 2012

REPOSITORIES: biostudies-literature

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Sonogashira-Hagihara reactions of halogenated glycals.

Koester Dennis C DC Werz Daniel B DB

Beilstein journal of organic chemistry 20120502

Herein, we report on our findings of the Sonogashira-Hagihara reaction with 1-iodinated and 2-brominated glycals using several aromatic and aliphatic alkynes. This Pd-catalyzed cross-coupling reaction presents a facile access to alkynyl C-glycosides and sets the stage for a reductive/oxidative refunctionalization of the enyne moiety to regenerate either C-glycosidic structures or pyran derivatives with a substituent in position 2. ...[more]

PMID: 23015813

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