Synthesis of Functionalized β-Keto Arylthioethers by the Aryne Induced [2,3] Stevens Rearrangement of Allylthioethers

Thangaraj, Manikandan ; Gaykar, Rahul N. ; Roy, Tony ; Biju, Akkattu T. (2017) Synthesis of Functionalized β-Keto Arylthioethers by the Aryne Induced [2,3] Stevens Rearrangement of Allylthioethers The Journal of Organic Chemistry, 82 (8). pp. 4470-4476. ISSN 0022-3263

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Official URL: http://doi.org/10.1021/acs.joc.7b00479

Related URL: http://dx.doi.org/10.1021/acs.joc.7b00479

Abstract

A mild and transition-metal-free synthesis of β-keto arylthioethers has been developed by the aryne triggered [2,3] Stevens rearrangement of allylthioethers. The key sulfur ylide intermediate for the rearrangement was formed by the S-arylation of allylthioethers with arynes generated from 2-(trimethylsilyl)aryl triflates using CsF. Later, the reaction products are converted into valuable heterocycles in two steps.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society
ID Code:128649
Deposited On:03 Nov 2022 06:50
Last Modified:03 Nov 2022 06:50

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