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Homolytic Substitution at Phosphorus for the Synthesis of Alkyl and Aryl Phosphanes
Author(s) -
Vaillard Santiago E.,
MückLichtenfeld Christian,
Grimme Stefan,
Studer Armido
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200701650
Subject(s) - homolysis , radical , alkyl , aryl , chemistry , reagent , substitution (logic) , primary (astronomy) , organic chemistry , medicinal chemistry , combinatorial chemistry , computer science , programming language , physics , astronomy
A transition‐metal‐free radical phosphonation using Me 3 SnPPh 2 and the less toxic Me 3 SiPPh 2 is reported. These readily available reagents react highly efficiently with primary and secondary alkyl radicals. Moreover, aryl radicals and tertiary alkyl radicals are phosphonated with Me 3 SnPPh 2 (see scheme; R=aryl, alkyl, vinyl; X=I, Br, OC(S)imidazolyl). DFT calculations provide insights into the mechanism of the reaction.
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