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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.

ABSTRACT: The hitherto unprecedented palladium-catalyzed cross-coupling of (Z)-?-bromo-?-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 ?-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.

SUBMITTER: Wang C 

PROVIDER: S-EPMC3781582 | biostudies-literature | 2010 Mar

REPOSITORIES: biostudies-literature

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

Wang Chao C   Xu Zhaoqing Z   Tobrman Tomas T   Negishi Ei-Ichi EI  

Advanced synthesis & catalysis 20100301 4

The hitherto unprecedented palladium-catalyzed cross-coupling of (<i>Z</i>)-β-bromo-β-arylethenylboranes can be made to proceed satisfactorily through (1) the use of highly catalytically active bis(tri-<i>tert</i>-butylphosphine)palladium or dichloro[<i>N</i>,<i>N</i>-bis-(2,6-diisopropylphenyl)imidazol-2-yl](<i>m</i>-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- a  ...[more]

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