Palladium-catalyzed C—P bond-forming reactions of aryl nonaflates accelerated by iodide

Mcerlain, H., Riley, L. M. and Sutherland, A. (2021) Palladium-catalyzed C—P bond-forming reactions of aryl nonaflates accelerated by iodide. Journal of Organic Chemistry, 86(23), pp. 17036-17049. (doi: 10.1021/acs.joc.1c02172) (PMID:34726917)

Abstract

An iodide-accelerated, palladium-catalyzed C–P bond-forming reaction of aryl nonaflates is described. The protocol was optimized for the synthesis of aryl phosphine oxides and was found to be tolerant of a wide range of aryl nonaflates. The general nature of this transformation was established with coupling to other P(O)H compounds for the synthesis of aryl phosphonates and an aryl phosphinate. The straightforward synthesis of stable, isolable aryl nonaflates, in combination with the rapid C–P bond-forming reaction allows facile preparation of aryl phosphorus target compounds from readily available phenol starting materials. The synthetic utility of this general strategy was demonstrated with the efficient preparation of an organic light-emitting diode (OLED) material and a phosphonophenylalanine mimic.

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Riley, Miss Leanne and Sutherland, Professor Andrew and Mcerlain, Miss Holly
• Authors: Mcerlain, H., Riley, L. M., and Sutherland, A.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Journal of Organic Chemistry
• Publisher: American Chemical Society
• ISSN: 0022-3263
• ISSN (Online): 1520-6904
• Published Online: 02 November 2021
• Copyright Holders: Copyright © 2021 The Authors
• First Published: First published in Journal of Organic Chemistry 86(23): 17036-17049
• Publisher Policy: Reproduced under a Creative Commons License

Project Code	Award No	Project Name	Principal Investigator	Funder's Name	Funder Ref	Lead Dept
172865		EPSRC DTP 16/17 and 17/18	Mary Beth Kneafsey	Engineering and Physical Sciences Research Council (EPSRC)	EP/N509668/1	Research and Innovation Services