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Reductive Rearrangement of Tetraphenyldiphosphine Disulfide To Trigger the Bisthiophosphinylation of Alkenes and Alkynes
Author(s) -
Sato Yuki,
Nishimura Misaki,
Kawaguchi Shinichi,
Nomoto Akihiro,
Ogawa Akiya
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201900073
Subject(s) - disulfide bond , chemistry , phosphorus , combinatorial chemistry , catalysis , reductive elimination , organic chemistry , biochemistry
Abstract The facile synthesis of organophosphorus compounds is of great importance for the development of new synthetic methods by using air‐stable sources of phosphorus. In this respect, a synthetic method that is based on a reductive rearrangement and is capable of converting air‐stable pentavalent phosphorus compounds into reactive trivalent phosphorus compounds is a powerful tool. Tetraphenyldiphosphine disulfide, which is a shelf‐stable solid, was the focus of this study, and it was shown to undergo reductive rearrangement to trigger the bisthiophosphinylation of a variety of alkenes, such as terminal, cyclic, internal, and branched alkenes, 1,3‐dienes, and terminal alkynes when exposed to light without any catalyst, base, or additive.