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Highly regio- and stereoselective phosphinylphosphination of terminal alkynes with tetraphenyldiphosphine monoxide under radical conditions.

ABSTRACT: The homolytic cleavage of the P^V(O)-P^III bond in tetraphenyldiphosphine monoxide simultaneously provides both pentavalent and trivalent phosphorus-centered radicals with different reactivities. The method using V-40 as an initiator is successfully investigated for the regio- and stereoselective phosphinylphosphination of terminal alkynes giving the corresponding trans-isomers of 1-diphenylphosphinyl-2-diphenylthiophosphinyl-1-alkenes in good yields. The protocol can be applied to a wide variety of terminal alkynes including both alkyl- and arylalkynes.

SUBMITTER: Tran DP

PROVIDER: S-EPMC8077611 | biostudies-literature | 2021

REPOSITORIES: biostudies-literature

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Highly regio- and stereoselective phosphinylphosphination of terminal alkynes with tetraphenyldiphosphine monoxide under radical conditions.

Tran Dat Phuc DP Sato Yuki Y Yamamoto Yuki Y Kawaguchi Shin-Ichi SI Kodama Shintaro S Nomoto Akihiro A Ogawa Akiya A

Beilstein journal of organic chemistry 20210420

The homolytic cleavage of the PV(O)-PIII bond in tetraphenyldiphosphine monoxide simultaneously provides both pentavalent and trivalent phosphorus-centered radicals with different reactivities. The method using V-40 as an initiator is successfully investigated for the regio- and stereoselective phosphinylphosphination of terminal alkynes giving the corresponding trans-isomers of 1-diphenylphosphinyl-2-diphenylthiophosphinyl-1-alkenes in good yields. The protocol can ...[more]

PMID: 33968259

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