Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 143, Issue 5, Pages 2178-2184Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c11119
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Funding
- Basic and Frontier Research Project of Chongqing [cstc2018jcyjAX0357, cstc2019jcyj-bshX0021]
- Fundamental Rese arch Funds for the Central Universities [2018CDXZ0003]
- NSFC [21901025, 21971028, 21772017, 21822303]
- China Postdoctoral Science Foundation [2018M640897]
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An unprecedented aryne 1,2,3,5-tetrasubstitution was achieved through a reaction involving 3-silylbenzyne and aryl allyl sulfoxide. The mechanism includes regioselective aryne insertion into the S=O bond, [3,6]-sigmatropic rearrangement, and thermal aromatic 1,3-silyl migration cascade.
Although benzyne has been well-known to serve as a synthon that can conveniently prepare various 1,2-difunctionalized benzenes, the sites other than its formal triple bond remain silent in typical benzyne transformations. An unprecedented aryne 1,2,3,5-tetrasubstitution was realized from 3-silylbenzyne and aryl allyl sulfoxide, the mechanistic pathway of which includes a regioselective aryne insertion into the S=O bond, a [3,6]-sigmatropic rearrangement, and a thermal aromatic 1,3-silyl migration cascade.
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