Highly regioselective hydroselenation of inactivated terminal alkynes using diselenide–Ph2P(O)H mixed systems under visible-light irradiation
摘要:
Upon visible-light irradiation, we could achieve a highly regioselective hydroselenation of inactivated terminal alkynes to give 1-(organylseleno)-1-alkenes by using diselenide-Ph2P(O)H mixed systems. The photoinduced hydroselenation presented in this study is advantageous as it does not involve the handling of oxygen-sensitive and foul-smelling selenols. (C) 2013 Elsevier Ltd. All rights reserved.
Diphenyl diselenide promotes the radicaladdition of benzeneselenol to inactivated acetylenes upon irradiation through Pyrex with a tungsten lamp. The addition may proceed by a radical chain mechanism that involves phenylseleno radical (PhSe·) as the key species, generated by the photolysis of (PhSe)2.