Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 17, Issue 42, Pages 11914-11918Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201101695
Keywords
asymmetric catalysis; enantioselectivity; Heck reaction; palladium; regioselectivity
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Funding
- Deutsche Forschungsgemeinschaft [Oe 249/5-1]
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2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) was employed as chiral ligand in the enantioselective intermolecular Mizoroki-Heck reaction, whereas the use of cognate BINAP(O) (monooxidized BINAP) is unprecedented. The regio- and enantioselectivity of the arylation of representative cyclic alkenes changes dramatically in the presence of hemilabile BINAP(O) instead of BINAP. The arylation of 2,3-dihydrofuran is perfectly regiodivergent (98:2 versus 0:100) and the arylation of cyclopentene is only enantioselective with BINAP(O) [60 versus 10% enantiomeric excess (ee)]. Use of [Pd-2(dba)(3)]center dot dba ( dba = dibenzylideneacetone) instead of Pd(OAc)(2) produces as high as 86% ee in the arylation of cyclopentene.
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