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Highly selective nickel-catalyzed gem-difluoropropargylation of unactivated alkylzinc reagents.

ABSTRACT: In spite of the important applications of difluoroalkylated molecules in medicinal chemistry, to date, the reaction of difluoroalkylating reagents with unactivated, aliphatic substrates through a controllable manner remains challenging and has not been reported. Here we describe an efficient nickel-catalyzed cross-coupling of unactivated alkylzinc reagen\ts with gem-difluoropropargyl bromides. The reaction proceeds under mild reaction conditions with high efficiency and excellent regiochemical selectivity. Transformations of the resulting difluoroalkylated alkanes lead to a variety of biologically active molecules, providing a facile route for applications in drug discovery and development. Preliminary mechanistic studies reveal that an alkyl nickel intermediate [Ni(tpy)alkyl] (tpy, terpyridine) is involved in the catalytic cycle.

SUBMITTER: An L

PROVIDER: S-EPMC5684216 | biostudies-literature | 2017 Nov

REPOSITORIES: biostudies-literature

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Highly selective nickel-catalyzed gem-difluoropropargylation of unactivated alkylzinc reagents.

An Lun L Xu Chang C Zhang Xingang X

Nature communications 20171113 1

In spite of the important applications of difluoroalkylated molecules in medicinal chemistry, to date, the reaction of difluoroalkylating reagents with unactivated, aliphatic substrates through a controllable manner remains challenging and has not been reported. Here we describe an efficient nickel-catalyzed cross-coupling of unactivated alkylzinc reagen\ts with gem-difluoropropargyl bromides. The reaction proceeds under mild reaction conditions with high efficiency and excellent regiochemical s ...[more]

PMID: 29133781

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