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Issue 22, 2014
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A facile and convenient sequential homobimetallic catalytic approach towards β-methylstyrenes. A one-pot Stille cross-coupling/isomerization strategy

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Abstract

An efficient one-pot synthetic approach towards β-methylstyrenes is reported. The transformation, based on sequential homobimetallic catalysis, involves a Stille cross-coupling reaction between aryl halides and allyltributylstannane, followed by an in situ palladium-catalyzed conjugative isomerization. The reaction was optimized, and the best results were obtained with 10 mol% Pd(PPh3)2Cl2, 8.0 equiv. LiCl, and 0.5 equiv. PPh3 in diglyme at 130 °C for 12 h. It was demonstrated that the reaction tolerates a wide variety of functional groups.

Graphical abstract: A facile and convenient sequential homobimetallic catalytic approach towards β-methylstyrenes. A one-pot Stille cross-coupling/isomerization strategy

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Publication details

The article was received on 20 Mar 2014, accepted on 14 Apr 2014 and first published on 15 Apr 2014


Article type: Paper
DOI: 10.1039/C4OB00604F
Citation: Org. Biomol. Chem., 2014,12, 3735-3743
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    A facile and convenient sequential homobimetallic catalytic approach towards β-methylstyrenes. A one-pot Stille cross-coupling/isomerization strategy

    S. O. Simonetti, E. L. Larghi and T. S. Kaufman, Org. Biomol. Chem., 2014, 12, 3735
    DOI: 10.1039/C4OB00604F

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