Journal
NATURE CATALYSIS
Volume 3, Issue 4, Pages 358-367Publisher
NATURE PUBLISHING GROUP
DOI: 10.1038/s41929-020-0425-1
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Funding
- NIH [1S10 OD020022-1, R01 GM126832, F32 GM129909]
- Jiangsu Province [BK20161307]
- Jiangsu Province (333 Talent Project)
- Huaiyin Normal University [JSKC18014]
- Merck
- University of Minnesota
- NSF [CHE-1048642]
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Cross-coupling reactions enable rapid, convergent synthesis of diverse molecules and provide the foundation for modern chemical synthesis. The most widely used methods employ sp(2)-hybridized coupling partners, such as aryl halides or related pre-functionalized substrates. Here, we demonstrate copper-catalysed oxidative cross-coupling of benzylic C-H bonds with alcohols to afford benzyl ethers, enabled by a redox buffering strategy that maintains the activity of the copper catalyst throughout the reaction. The reactions employ the C-H substrate as the limiting reagent and exhibit broad scope with respect to both coupling partners. This approach to direct site-selective functionalization of C(sp(3))-H bonds provides the basis for efficient three-dimensional diversification of organic molecules and should find widespread utility in organic synthesis, particularly for medicinal chemistry applications.
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