Gold(I)-Mediated Hydrothiolation of Conjugated Olefins

Abstract

Thiol additions to conjugated olefins were catalyzed by Ph₃PAuBF₄ with excellent yields at room temperature. A variety of functionalized thiols, with both electron-donating and electron-withdrawing substituents, are compatible with this system. Hydrothiolations of 1,3-cyclohexadiene were also achieved in similar yields at 50 °C.

Key words

gold - homogeneous catalysis - hydrothiolation - conjugated olefin

References and Notes

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15

For thoroughness, all reactions were conducted overnight, but complete conversions were typically achieved in one hour.

17

Indene was chosen because the two benzylic protons at C1 are enantiotopic with respect to added deuterium.