期刊
CHEMICAL SCIENCE
卷 7, 期 8, 页码 5260-5264出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6sc01087c
关键词
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资金
- Indiana University-Purdue University Indianapolis
- NSF [CHE-1350541]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1350541] Funding Source: National Science Foundation
Copper-promoted direct carbonylation of unactivated sp(3)C-H and aromatic sp(2)C-H bonds of amides was developed using nitromethane as a novel carbonyl source. The sp(3)C-H functionalization showed high site-selectivity by favoring the C-H bonds of alpha-methyl groups. The sp(2)C-H carbonylation featured high regioselectivity and good functional group compatibility. Kinetic isotope effect studies indicated that the sp(3)C-H bond breaking step is reversible, whereas the sp(2)C-H bond cleavage is an irreversible but not the rate-determining step. Control experiments showed that a nitromethyl intermediate should be involved in the present reaction.
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