2, 2′‐Azobis(2‐methylpropionitrile)‐Mediated Alkyne Hydrostannylation: Reaction Mechanism1. Issue 43 (2nd September 2013)

• Record Type: Journal Article
• Authors: Oderinde, Martins S.; Froese, Robert D. J.; Organ, Michael G.
• Is Part Of: Angewandte Chemie international edition. Volume 52:Issue 43(2013)
• Page Start: 11334
• Page End: 11338
• Publication Date: 2013-09-02
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201303736
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="graphical" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <p> <bold>Not as radical as you think</bold>: 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).<boxed-text content-type="graphic" position="anchor" orientation="portrait"><graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgg4t3crvv0" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /></boxed-text></p> </abstract>