Vinylchloride is one of the most important structure moieties among the chlorine containing compounds. On the one hand, they are widely found in natural products, pharmaceuticals and agrochemicals. On the other hand, the development of coupling reaction such as Buchwald-Hartwig amination and Suzuki-Miyaura coupling made the vinylchloride building blocks highly desirable in organic transformation. Although many methodologies have been developed for synthesis of vinylchlorides through hydrochlorination of alkynes, the direct hydrochlorination of unactivated alkynes using HCl as chlorine source was rarely reported. Therefore, a novel chlorinating reagent was developed, which can be easily applied for synthesis of such vinylchloride compunds with commercially available gold nanoparticles as catalyst. A wide range of functional groups could be tolerated in this transformation and high regioselectivity was also achieved.

Highly regioselective hydrochlorination of alkynes with a novel chlorinating reagent

254th National Meeting (2017)

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