Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 143, Issue 36, Pages 14438-14444Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.1c07117
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Funding
- NIH [R35 GM134929, S10 OD020022]
- NSF [CHE-1048642]
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This study presents a copper-catalyzed method for site-selective cross-coupling of pyrazoles and other N-H heterocycles with substrates bearing (hetero)benzylic C-H bonds. The strategy achieves excellent N-site selectivity controlled by co-catalytic additives, allowing broad scope for complex molecule synthesis and medicinal chemistry application.
Azoles are important motifs in medicinal chemistry, and elaboration of their structures via direct N-H/C-H coupling could have broad utility in drug discovery. The ambident reactivity of many azoles, however, presents significant selectivity challenges. Here, we report a copper-catalyzed method that achieves site-selective cross-coupling of pyrazoles and other N-H heterocycles with substrates bearing (hetero)benzylic C-H bonds. Excellent N-site selectivity is achieved, with the preferred site controlled by the identity of co-catalytic additives. This cross-coupling strategy features broad scope for both the N-H heterocycle and benzylic C-H coupling partners, enabling application of this method to complex molecule synthesis and medicinal chemistry.
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