Highly regioselective simultaneous introduction of phosphino and seleno groups into unsaturated bonds by the novel combination of (Ph2P)2 and (PhSe)2 upon photoirradiation.

[摘要]：Prepn. of b-selenoether-functionalized phosphines was achieved by chemoselective radical addn. of (Ph2P)2/(PhSe)2 mixt. to alkenes, alkynes and allenes under UV-irradn. Addn. of (Ph2P)2/(PhSe)2 to RCYCH followed by oxidn. gave (E)-RC[P(O)Ph2]:CHSePh (5a-f; R = 4-CF3C6H4, Ph, 4-BrC6H4, 4-MeOC6H4, 4-C5H11C6H4, 1-cyclohexenyl), the same procedure for allenes R1CH:C:CH2 and cyclo-C6H10:C:CH2 afforded (Z)-R1CH:C(SePh)CH2P(O)Ph2 (8a-e; R1 = cyclohexyl, tBu, PhCH2, Ph), whereas 1,2-cyclononadiene was found to be unreactive. The diphosphine-diselenide combination attains simultaneous introduction of diphenylphosphino and phenylseleno groups into carbon-carbon unsatd. bonds such as terminal alkynes or allenes, regioselectively.

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