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Adv Synth Catal. 2010 Mar 8;352(4):627-631.

Arylethyne Bromoboration-Negishi Coupling Route to E- or Z-Aryl-Substituted Trisubstituted Alkenes of ≥98% IsomericPurity. New Horizon in the Highly Selective Synthesis of Trisubstituted Alkenes.

Author information

1
Herbert C. Brown Laboratories of Chemistry, Purdue University, 560 Oval Dr., West Lafayette, IN 47907-2084, USA.

Abstract

The hitherto unprecedented palladium-catalyzed cross-coupling of (Z)-β-bromo-β-arylethenylboranes can be made to proceed satisfactorily through (1) the use of highly catalytically active bis(tri-tert-butylphosphine)palladium or dichloro[N,N-bis-(2,6-diisopropylphenyl)imidazol-2-yl](m-chloropyridine)palladium and (2) conversion of dibromoboryl group to (pinacol)boryl group. Thus, a wide variety of carbon groups can be used to substitute bromine in ≥98% stereo- and regioselectivity, while suppressing the otherwise dominant β-debromoboration. Together with the alkylethyne-based protocols, the alkyne bromoboration-Negishi coupling tandem process has emerged as the most widely applicable and highly selective route to trisubstituted alkenes including those that are otherwise difficult to access.

KEYWORDS:

(Z)-β-bromo-β-arylethenylboranes; Negishi coupling; arylethyne bromoboration; bis(tri-tert-butylphosphine)palladium; dichloro[N,N-bis-(2,6-diisopropylphenyl)imidazol-2-yl](m-chloropyridine)palladium

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