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

Lun An, Chang Xu and Xingang Zhang ()
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Lun An: Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences
Chang Xu: Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences
Xingang Zhang: Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences

Nature Communications, 2017, vol. 8, issue 1, 1-9

Abstract: 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.

Date: 2017
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DOI: 10.1038/s41467-017-01540-1

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