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Multimetallic catalysed radical oxidative C(sp3)–H/C(sp)–H cross-coupling between unactivated alkanes and terminal alkynes

Shan Tang, Pan Wang, Haoran Li and Aiwen Lei ()
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Shan Tang: College of Chemistry and Molecular Sciences, Institute for Advanced Studies (IAS), Wuhan University
Pan Wang: College of Chemistry and Molecular Sciences, Institute for Advanced Studies (IAS), Wuhan University
Haoran Li: College of Chemistry and Molecular Sciences, Institute for Advanced Studies (IAS), Wuhan University
Aiwen Lei: College of Chemistry and Molecular Sciences, Institute for Advanced Studies (IAS), Wuhan University

Nature Communications, 2016, vol. 7, issue 1, 1-8

Abstract: Abstract Radical involved transformations are now considered as extremely important processes in modern organic synthetic chemistry. According to the demand by atom-economic and sustainable chemistry, direct C(sp3)–H functionalization through radical oxidative coupling represents an appealing strategy for C–C bond formations. However, the selectivity control of reactive radical intermediates is still a great challenge in these transformations. Here we show a selective radical oxidative C(sp3)–H/C(sp)–H cross-coupling of unactivated alkanes with terminal alkynes by using a combined Cu/Ni/Ag catalytic system. It provides a new way to access substituted alkynes from readily available materials. Preliminary mechanistic studies suggest that this reaction proceeds through a radical process and the C(sp3)–H bond cleavage is the rate-limiting step. This study may have significant implications for controlling selective C–C bond formation of reactive radical intermediates by using multimetallic catalytic systems.

Date: 2016
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DOI: 10.1038/ncomms11676

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