1241903-46-7Relevant articles and documents
Arylethyne bromoboration-Negishi coupling route to E- Or Z-aryl-substituted trisubstituted alkenes of ≥ 98% isomeric purity. New horizon in the highly selective synthesis of trisubstituted alkenes
Wang, Chao,Xu, Zhaoqing,Tobrman, Tomas,Negishi, Ei-Ichi
, p. 627 - 631 (2010)
The hitherto unprecedented palladiumcatalyzed 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 the dibromoboryl group to the (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.
