Highly Regioselective Simultaneous Introduction of Phosphino and Seleno Groups into Unsaturated Bonds by the Novel Combination of (Ph₂P)₂and (PhSe)₂upon Photoirradiation

Abstract

A novel combination of tetraphenyldiphosphine and diphenyl diselenide under photoirradiation conditions attains simultaneous introduction of diphenylphosphino and phenylseleno groups into carbon-carbon unsaturated bonds such as terminal alkynes or allenes, regioselectively.

Organometallic Approaches to Carbon–Sulfur Bond Formation

“…A few key recent discoveries are highlighted below. For related reactions, see the following references [165,168,197,[236][237][238][239][240][241][242][243].…”

Applications of Diphosphines in Radical Reactions

“…The same thiophosphination product ( 7 ) can be synthesized by the radical addition of Ph 2 P−SPh to alkynes, reported by Yorimitsu, Oshima et al . Using diphenyl diselenide instead of disulfide also gives the corresponding 1‐seleno‐2‐phosphinoalkenes ( 8 ) in good yields . When diphenyl ditelluride was used, the regioselectivity was completely exchanged, and adduct ( 6 ) was obtained in which a tellurium functional group was introduced into the inner carbon and a phosphorus group was introduced into the terminal carbon simultaneously .…”

“…Among the systems that combine diphosphines and dichalcogenides, only the combination of diphosphines and diselenides can be used to add to an allene in good yield with excellent regioselectivity. In this case, the phosphino group is selectively introduced onto the terminal carbon, and the seleno group onto the central carbon (Scheme ) . The combination of diphosphine and disulfide afforded complex mixtures because the capturing ability of the generated carbon radical is low.…”

Simultaneous Construction of C−Se And C−S Bonds via the Visible‐Light‐Mediated Multicomponent Cascade Reaction of Diselenides, Alkynes, and SO2

“…Sun and co‐workers reported a radical‐initiated selenodifluoromethylation of alkenes promoted by copper salt . Ogawa's group developed multicomponent cascade reactions of diselenide, alkyne with alkene, benzoyl peroxide, and (Ph 2 P) 2 (Scheme a). The multicomponent cascede reactions induced by selenium radical are effective in synthesizing organoselenium compounds.…”