Direct Aerobic Carbonylation of C(sp2)–H and C(sp3)–H Bonds through Ni/Cu Synergistic Catalysis with DMF as the Carbonyl Source | Zendy

Xuesong Wu | Zendy; Yan Zhao | Zendy; Haibo Ge | Zendy

Open Access

Direct Aerobic Carbonylation of C(sp²)–H and C(sp³)–H Bonds through Ni/Cu Synergistic Catalysis with DMF as the Carbonyl Source

Author(s) -

Xuesong Wu,

Yan Zhao,

Haibo Ge

Publication year - 2015

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.5b01671

Subject(s) - chemistry , carbonylation , catalysis , regioselectivity , surface modification , medicinal chemistry , nickel , methylene , denticity , selectivity , copper , methyl group , stereochemistry , organic chemistry , carbon monoxide , group (periodic table) , crystal structure

The direct carbonylation of aromatic sp(2) and unactivated sp(3) C-H bonds of amides was achieved via nickel/copper catalysis under atmospheric O2 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 α-methyl groups over those of the α-methylene, β- or γ-methyl groups. Moreover, this reaction showed a predominant preference for functionalizing the α-methyl over α-phenyl group. Mechanistic studies revealed that nickel/copper synergistic catalysis is involved in this process.

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