Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 73, Issue 6, Pages 2292-2301Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo702542a
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Funding
- NIGMS NIH HHS [1R01 GM067610, R01 GM067610-05, R01 GM067610] Funding Source: Medline
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Hypophosphorous compounds (MOP(O)H-2, M = H, R3NH) 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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