Aryne 1,2,3,5-Tetrasubstitution Enabled by 3-Silylaryne and Allyl Sulfoxide via an Aromatic 1,3-Silyl Migration

• DOI: 10.1021/jacs.0c11119
• Publication Date: 2021-01-29T00:58:09Z
• Authors: Jiarong Shi; Lianggui Li; Chunhui Shan; Junli Wang; Zhonghong Chen; Rongrong Gu; Jia He; Min Tan; Yu Lan; Yang Li
• Keywords: Aryne; Synthon; Sulfoxide

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 transformations. An unprecedented aryne 1,2,3,5-tetrasubstitution was realized from 3-silylbenzyne and aryl allyl sulfoxide, mechanistic pathway of which includes regioselective insertion into S═O bond, [3,6]-sigmatropic rearrangement, thermal aromatic 1,3-silyl migration cascade.