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Bimetallic Radical Redox-Relay Catalysis for the Isomerization of Epoxides to Allylic Alcohols

preprint
submitted on 23.05.2019 and posted on 24.05.2019 by Ke-Yin Ye, Terry McCallum, Song Lin
Organic radicals are generally short-lived intermediates with exceptionally high reactivity. Strategically, achieving synthetically useful transformations mediated by organic radicals requires both efficient initiation and selective termination events. Here, we report a new catalytic strategy, namely bimetallic radical redox-relay, in the regio- and stereoselective rearrangement of epoxides to allylic alcohols. This approach exploits the rich redox chemistry of Ti and Co complexes and merges reductive epoxide ring opening (initiation) with hydrogen atom transfer (termination). Critically, upon effecting key bond-forming and -breaking events, Ti and Co catalysts undergo proton-transfer/electron-transfer with one another to achieve turnover, thus constituting a truly synergistic dual catalytic system.

Funding

Cornell University

History

Email Address of Submitting Author

songlin@cornell.edu

Institution

Cornell University

Country

United States

ORCID For Submitting Author

0000-0002-8880-6476

Declaration of Conflict of Interest

No conflict of interest

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