Selective Aryne Formation via Grob Fragmentation from the [2+2] Cycloadducts of 3-Triflyloxyarynes

Jiarong Shi; Hai Xu; Dachuan Qiu; Jia He; Yang Li

doi:10.1021/jacs.6b12161

Selective Aryne Formation via Grob Fragmentation from the [2+2] Cycloadducts of 3-Triflyloxyarynes

J Am Chem Soc. 2017 Jan 18;139(2):623-626. doi: 10.1021/jacs.6b12161. Epub 2017 Jan 10.

Authors

Jiarong Shi¹, Hai Xu¹, Dachuan Qiu¹, Jia He¹, Yang Li¹

Affiliation

¹ School of Chemistry and Chemical Engineering, Chongqing University , 174 Shazheng Street, Chongqing 400030, P. R. China.

PMID: 28038312
DOI: 10.1021/jacs.6b12161

Abstract

A chemoselective ring-opening protocol of the formal [2+2] cycloadducts of 3-triflyloxyarynes was developed to generate 2,3-aryne intermediate via Grob fragmentation. A variety of 1,3-di- and 1,2,3-trisubstituted arenes could be readily accessed through this [2+2] cycloaddition-2,3-aryne formation sequence. The regioselectivity in these transformations originates from the steric repulsion of the aliphatic chain.

Publication types

Research Support, Non-U.S. Gov't