期刊
ACS CATALYSIS
卷 5, 期 2, 页码 1164-1171出版社
AMER CHEMICAL SOC
DOI: 10.1021/cs501502u
关键词
nickel; Sonogashira coupling alkynylation; pincer complex; kinetics; alkylation
资金
- EPFL
- Swiss National Science Foundation [200020_144393/1]
- Swiss National Science Foundation (SNF) [200020_144393] Funding Source: Swiss National Science Foundation (SNF)
Direct coupling of alkyl halides with terminal alkynes provides an efficient and streamlined access to alkyl-substituted alkynes, which are important synthetic intermediates, biologically active molecules, and organic materials. However, until now,there have been fewer than a handful of catalytic methods available for this reaction, and detailed mechanistic studies have not been reported. Herein, we describe the design and development a new nickel pincer complex that catalyzes the direct coupling of primary alkyl halides with terminal alkynes at room temperature. The catalysis has a good substrate scope and high functional group tolerance. Kinetic data suggest that the new pincer ligand is hemilabile, and the dissociation of a labile amine donor is the (t)urnover-determining step of the catalysis. An intermediate Ni-alkynyl species has been isolated and structurally characterized. The reactivity of this species gives insight into the nature of the active species for the activation of alkyl halide.
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