Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 35, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202207150
Keywords
Alcohols; Conjugate Addition; Deoxygenation; Photoredox
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Funding
- National Institute of General Medical Sciences (NIGMS), the NIH [R35GM134897-03]
- Princeton Catalysis Initiative
- Princeton University
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In this paper, a convenient catalytic method for the coupling of alcohols with alkenes under mild photocatalytic conditions using N-heterocyclic carbene (NHC)-mediated deoxygenative Giese-type addition is described. This method is applicable to a wide range of alcohol compounds and allows for late-stage diversification reactions, showing significant potential for various applications.
The rapid exploration of sp(3)-enriched chemical space is facilitated by fragment-coupling technologies that utilize simple and abundant alkyl precursors, among which alcohols are a highly desirable, commercially accessible, and synthetically versatile class of substrate. Herein, we describe an operationally convenient, N-heterocyclic carbene (NHC)-mediated deoxygenative Giese-type addition of alcohol-derived alkyl radicals to electron-deficient alkenes under mild photocatalytic conditions. The fragment coupling accommodates a broad range of primary, secondary, and tertiary alcohol partners, as well as structurally varied Michael acceptors containing traditionally reactive sites, such as electrophilic or oxidizable moieties. We demonstrate the late-stage diversification of densely functionalized molecular architectures, including drugs and biomolecules, and we further telescope our protocol with metallaphotoredox cross-coupling for step-economic access to sp(3)-rich complexity.
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