Journal
ACS CATALYSIS
Volume 10, Issue 20, Pages 11841-11847Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.0c03697
Keywords
photoredox; chromium; dual catalysis; diols; hydroxyallylation
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Funding
- Deutsche Forschungsgemeinschaft (Leibniz Award)
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Herein, we present a dual catalytic strategy to efficiently obtain monoprotected homoallylic 1,2-diols by coupling abundant aldehydes with simple (silyl) enol ethers, thus providing direct access to this important motif without the (super) stoichiometric use of prefunctionalized metal-allyl species. The modularity of our approach is shown by the introduction of several silyl- and alkyl-based protecting groups. To highlight functional group tolerance and chemoselectivity, we demonstrate the functionalization of a variety of aliphatic and (hetero)aromatic aldehydes, even in the presence of ketones and esters. Mechanistic studies support a radical mechanism, starting from the single electron oxidation of the enol ether.
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