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- Title
Esters as Radical Acceptors: β‐NHC‐Borylalkenyl Radicals Induce Lactonization by C−C Bond Formation/Cleavage on Esters.
- Authors
Shimoi, Masaki; Maeda, Katsuhiro; Geib, Steven J.; Curran, Dennis P.; Taniguchi, Tsuyoshi
- Abstract
Substituted propargyl acetates are converted into 4‐boryl‐2(5H)‐furanones upon thermolysis in the presence of an N‐heterocyclic carbene borane (NHC‐borane) and di‐tert‐butyl peroxide. The acetyl methyl group is lost during the reaction as methane. Evidence suggests that the reaction proceeds by a sequence of radical events including: 1) addition of an NHC‐boryl radical to the triple bond; 2) cyclization of the resultant β‐borylalkenyl radical to the ester carbonyl group; 3) β‐scission of the so‐formed alkoxy radical to provide the 4‐boryl‐2(5H)‐furanone and a methyl radical; and 4) hydrogen abstraction from the NHC‐borane to return the initial NHC‐boryl radical and methane.
- Subjects
ESTERS; RADICALS; ALDEHYDES; KETONES; LACTONES
- Publication
Angewandte Chemie, 2019, Vol 131, Issue 19, p6423
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201902001