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Palladium-Catalyzed Cyanothiolation of Internal Alkynes Using Organic Disulfides and tert-Butyl Isocyanide

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journal contribution
posted on 2018-04-03, 00:00 authored by Shinya Higashimae, Daichi Kurata, Shin-ichi Kawaguchi, Shintaro Kodama, Motohiro Sonoda, Akihiro Nomoto, Akiya Ogawa
Despite the availability of selective synthetic approaches to multifunctionalized substituted olefins, the cyanothiolation of internal alkynes has been much less explored. Herein, we show that nonactivated internal alkynes can be successfully cyanothiolated with diaryl disulfides and tert-butyl isocyanide in the presence of a Pd catalyst (e.g., Pd­(PPh3)4) with the release of isobutene and arenethiol to afford β-thiolated alkenyl cyanides in yields of 34–89%.