ortho-Difunctionalization of arynes by LiZnEt2(TMP)-mediated deprotonative zincation/elimination of aryl triflates

Journal Article (Journal Article)

Generation of arynes from aryl triflates has been achieved using lithium diethyl(tetramethylpiperidyl)-zincate base LiZnEt2(TMP), via a directed ortho-deprotonative zincation and subsequent elimination of the triflate group. The aryne formation has been demonstrated by the cycloaddition reaction with diene and insertion reactions with ureas. Furthermore, the nucleophilic addition of LiZnEt2(TMP) to arynes was observed in the absence of external aryne partners, offering a new cascade strategy for diverse difunctionalization of arynes.

Full Text

Duke Authors

Cited Authors

  • Cho, S; Wang, Q

Published Date

  • June 28, 2018

Published In

Volume / Issue

  • 74 / 26

Start / End Page

  • 3325 - 3328

Electronic International Standard Serial Number (EISSN)

  • 1464-5416

International Standard Serial Number (ISSN)

  • 0040-4020

Digital Object Identifier (DOI)

  • 10.1016/j.tet.2018.03.044

Citation Source

  • Scopus