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  • Title: Clean inversion of configuration in the Pd-catalyzed cross-coupling of 2-bromo-1,3-dienes.
    Author: Zeng X, Hu Q, Qian M, Negishi E.
    Journal: J Am Chem Soc; 2003 Nov 12; 125(45):13636-7. PubMed ID: 14599182.
    Abstract:
    The Pd-catalyzed cross-coupling reaction of 2-bromo-1,3-dienes derived from alkyl aldehydes, especially with Cl2Pd(DPEphos) as a catalyst, proceeds with clean stereoinversion of the Br-bearing C=C bond to produce in high yields and in high stereoselectivity (>/=97-98%) conjugated Z,E dienes of potentially high utility in the synthesis of complex natural products. The observed stereoinversion cannot be readily accommodated by the widely accepted pi-sigma-pi rearrangement mechanism for isomerization of ordinary allylpalladium derivatives.
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