Abstract
The reaction of 2,2-diphenylhepta-4,5-dien-1-ol (4) with (L)AuOTs [L = P(t-Bu)2o-biphenyl] and the reactions of 2,2-diphenylhepta-5,6-dien-1-ol (10) with either (L)AuOTs or (L)AuCl/AgSbF6 have been investigated. For both substrates, the mono(gold) vinyl complexes generated via C–O bond formation have been independently synthesized, and the protodeauration behavior has been investigated. Analysis of the reaction of 4 with (L)AuOTs supported a mechanism involving rapid and reversible C–O bond formation followed by rate-limiting and stereochemically determining protodeauration. Analysis of the reaction of 10 with (L)AuOTs was in accord with irreversible C–O bond formation followed by rapid auration of the resulting mono(gold) vinyl complex. In comparison, analysis of the reaction of 10 with (L)AuCl/AgSbF6 pointed to a mechanism involving rate-limiting C–O bond formation followed by rapid protodeauration of the resulting mono(gold) vinyl complex without competitive auration.
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