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2,2′‐Azobis(2‐methylpropionitrile)‐Mediated Alkyne Hydrostannylation: Reaction Mechanism
Author(s) -
Oderinde Martins S.,
Froese Robert D. J.,
Organ Michael G.
Publication year - 2013
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.201303736
Subject(s) - alkyne , chemistry , mechanism (biology) , radical , photochemistry , organic chemistry , catalysis , philosophy , epistemology
Not as radical as you think : The free‐radical hydrostannylation of alkynes has been extensively studied and while every published mechanism involves solely radical intermediates, this appears not to be correct. Trace molecular oxygen is necessary for any radical‐mediated hydrostannylation to occur with a wide selection of alkynes, thus leading to a proposed hybrid single‐electron transfer/radical propagation mechanism. AIBN=2,2′‐azobis(2‐methylpropionitrile).