Vitamin B₁₂ and hydrogen atom transfer cooperative catalysis as a hydride nucleophile mimic in epoxide ring opening.

ABSTRACT: Epoxide ring-opening reactions have long been utilized to furnish alcohol products that are valuable in many subfields of chemistry. While many epoxide-opening reactions are known, the hydrogenative opening of epoxides via ionic means remains challenging because of harsh conditions and reactive hydride nucleophiles. Recent progress has shown that radical chemistry can achieve hydrogenative epoxide ring opening under relatively mild conditions; however, these methods invariably require oxophilic metal catalysts and sensitive reagents. In response to these challenges, we report a new approach to epoxide ring-opening hydrogenation using bio-inspired Earth-abundant vitamin B₁₂ and thiol-centric hydrogen atom transfer (HAT) co-catalysis to produce Markovnikov alcohols under visible l

SUBMITTER: Funk BE 

PROVIDER: S-EPMC10210593 | biostudies-literature | 2023 Apr

REPOSITORIES: biostudies-literature