Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 1, Pages 197-202Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201910602
Keywords
alcohols; copper; oxidation; photocatalysis; radicals
Categories
Funding
- NIH [GM095666]
Ask authors/readers for more resources
Methods that enable the direct C-H alkoxylation of complex organic molecules are significantly underdeveloped, particularly in comparison to analogous strategies for C-N and C-C bond formation. In particular, almost all methods for the incorporation of alcohols by C-H oxidation require the use of the alcohol component as a solvent or co-solvent. This condition limits the practical scope of these reactions to simple, inexpensive alcohols. Reported here is a photocatalytic protocol for the functionalization of benzylic C-H bonds with a wide range of oxygen nucleophiles. This strategy merges the photoredox activation of arenes with copper(II)-mediated oxidation of the resulting benzylic radicals, which enables the introduction of benzylic C-O bonds with high site selectivity, chemoselectivity, and functional-group tolerance using only two equivalents of the alcohol coupling partner. This method enables the late-stage introduction of complex alkoxy groups into bioactive molecules, providing a practical new tool with potential applications in synthesis and medicinal chemistry.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available