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33.2.5.1.5.3 Variation 3: Addition of Diselenides

DOI: 10.1055/sos-SD-033-00348

Avilov, D.; Dittmer, D.Science of Synthesis, (200733289.

The addition of diselenides to alkynes, which leads to 1,2-bis(organoselanyl)alkenes 48, can proceed by nucleophilic,[‌138‌‌140‌] radical, or metal-catalyzed mechanisms. Radical addition of diaryl diselenides to alkynes, which may be initiated either thermally or by UV irradiation, leads to mixtures of E- and Z-1,2-bis(arylselanyl)alkenes in ratios of 95:5 to 17:83; the E-isomer is usually the major product although the stereoselectivity is often moderate (Scheme 23).[‌141‌‌143‌]

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