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  • Title: Palladium-catalyzed reactions of hypophosphorous compounds with allenes, dienes, and allylic electrophiles: methodology for the synthesis of allylic h-phosphinates.
    Author: Bravo-Altamirano K, Abrunhosa-Thomas I, Montchamp JL.
    Journal: J Org Chem; 2008 Mar 21; 73(6):2292-301. PubMed ID: 18275217.
    Abstract:
    Hypophosphorous compounds (MOP(O)H(2), M = H, R(3)NH) effectively participate in metal-catalyzed C-P bond-forming reactions with allenes, dienes, and activated allylic electrophiles under mild conditions. The catalytic system Pd(2)dba(3)/xantphos is crucial to avoid or minimize the competitive reductive transfer-hydrogenation pathway available to hypophosphorous acid derivatives. Further investigation into the allylation mechanism provided access to the analogy allylic acetate-allylic phosphinate, which then led to the development of a Pd-catalyzed rearrangement of preformed allylic phosphinates esters and, ultimately, to a catalytic dehydrative allylation of hypophosphorous acid with allylic alcohols. The reactions disclosed herein constitute efficient synthetic approaches, not only to prepare allylic H-phosphinic acids but also their esters via one-pot tandem processes. In addition, the potential of H-phosphinates as useful synthons for the preparation of other organophosphorus compounds is demonstrated.
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