期刊
JOURNAL OF ORGANOMETALLIC CHEMISTRY
卷 687, 期 2, 页码 518-524出版社
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jorganchem.2003.09.008
关键词
Pd-catalyzed tandem cross-coupling; arylation-alkylation; 1,1-dihalo-1-alkenes; alpha-alkyl-substituted styrenes; aryl- and alkylzincs
Trans-selective monoarylation of 1, 1-dibromo- and 1,1-dichloro-1-alkenes (1) can be achieved in > 80% yields and in > 98-99% stereo selectivity with arylzinc bromides in the presence of a catalytic amount of Cl2Pd(DPEphos) or Cl2Pd(dppb), the former permitting cleaner and higher yielding reactions. Although THF is a generally satisfactory solvent, ether and toluene are superior to THF in some cases. The second substitution of (Z)-alpha-bromostyrenes (3) with alkylzincs in the presence of 2 mol% of Pd('Bu3P)(2) proceeds to give the corresponding 2 in >90% yields and in greater than or equal to98-99% stereoselectivity. Although somewhat less satisfactory, the use of Cl2Pd(DPEphos) permits a one-pot tandem arylation-alkylation. (C) 2003 Elsevier B.V. All rights reserved.
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