Copper-promoted site-selective carbonylation of sp3 and sp2 C-H bonds with nitromethane

Xuesong Wu, Jinmin Miao, Yanrong Li, Guigen Li, Haibo Ge

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26 Scopus citations

Abstract

Copper-promoted direct carbonylation of unactivated sp3 C-H and aromatic sp2 C-H bonds of amides was developed using nitromethane as a novel carbonyl source. The sp3 C-H functionalization showed high site-selectivity by favoring the C-H bonds of α-methyl groups. The sp2 C-H carbonylation featured high regioselectivity and good functional group compatibility. Kinetic isotope effect studies indicated that the sp3 C-H bond breaking step is reversible, whereas the sp2 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.

Original languageEnglish
Pages (from-to)5260-5264
Number of pages5
JournalChemical Science
Volume7
Issue number8
DOIs
StatePublished - 2016

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