Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 15, Pages 4924-4927Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b01671
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Funding
- NSF [CHE-1350541]
- Indiana University-Purdue University Indianapolis
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1350541] Funding Source: National Science Foundation
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The direct carbonylation of aromatic sp(2) and unactivated sp3 C-H bonds of amides was achieved via nickel/copper catalysis under atmospheric O-2 with the assistance of a bidentate directing group. The sp(2) C-H functionalization showed high regioselectivity and good functional group compatibility. The sp(3) C-H functionalization showed high site-selectivity by favoring the C-H bonds of alpha-methyl groups over those of the alpha-methylene, beta- or gamma-methyl groups. Moreover, this reaction showed a predominant preference for functionalizing the alpha-methyl over alpha-phenyl group. Mechanistic studies revealed that nickel/copper synergistic catalysis is involved in this process.
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