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Issue 39, 2018
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Addition of arylstannanes to alkynes giving ortho-alkenylarylstannanes catalysed cooperatively by a rhodium complex and zinc chloride

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Abstract

The reaction of arylstannanes ArSnR3 with unfunctionalised alkynes was found to proceed in the presence of a rhodium catalyst and a catalytic amount of zinc chloride to give ortho-alkenylarylstannanes with high selectivity in high yields. The catalytic cycle is very unique, consisting of three transmetalation steps, from Sn to Rh, Rh to Zn, and Zn to Sn, in addition to arylrhodation of alkyne followed by 1,4-migration of Rh from 2-arylalkenyl carbon to ortho-alkenylaryl carbon.

Graphical abstract: Addition of arylstannanes to alkynes giving ortho-alkenylarylstannanes catalysed cooperatively by a rhodium complex and zinc chloride

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Publication details

The article was received on 05 Jun 2018, accepted on 10 Aug 2018 and first published on 17 Aug 2018


Article type: Edge Article
DOI: 10.1039/C8SC02459F
Chem. Sci., 2018,9, 7700-7704
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    Addition of arylstannanes to alkynes giving ortho-alkenylarylstannanes catalysed cooperatively by a rhodium complex and zinc chloride

    J. Ming, Q. Shi and T. Hayashi, Chem. Sci., 2018, 9, 7700
    DOI: 10.1039/C8SC02459F

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