Work

Silylaryl Halides Can Replace Triflates as Aryne Precursors

Year: 2016

Type: article

Abstract: Silylaryl bromides and iodides can be prepared in one step from commercially available starting materials. Arynes can be generated from these compounds under conditions nearly identical to those employed for silylaryl triflates. Three distinct transformations, ortho-arylation of N-tritylanilines, intermolecular addition of arynes to amides, and reaction of ureas with arynes, were shown to be successful for the new aryne precursors. The main advantage of silylaryl halides relative to silyl aryl triflates is their one-step preparation from commercially available starting materials.

Source: Organic Letters

DOI: 10.1021/acs.orglett.6b01952

Authors: Milad Mesgar, Olafs Daugulis

Institution: University of Houston

Language: English

Topic: Cyclization and Aryne Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Welch Foundation, National Institute of General Medical Sciences

Awards: G2854228422, New Methods for Direct Carbon-Hydrogen Bond Functionalization