Arsenous chloride-free synthesis of cyclic tertiary organoarsines from arylarsine oxides and di-Grignard reagents

Aaron M. Gregson; Steven M. Wales; Stephen J. Bailey; Paul A. Keller

doi:10.1016/j.jorganchem.2015.03.006

Back

Arsenous chloride-free synthesis of cyclic tertiary organoarsines from arylarsine oxides and di-Grignard reagents

Journal article

Peer reviewed

Arsenous chloride-free synthesis of cyclic tertiary organoarsines from arylarsine oxides and di-Grignard reagents

Aaron M. Gregson, Steven M. Wales, Stephen J. Bailey and Paul A. Keller

Journal of Organometallic Chemistry, Vol.785, pp.77-83

2015

DOI: https://doi.org/10.1016/j.jorganchem.2015.03.006

Files and links (1)

url

https://doi.org/10.1016/j.jorganchem.2015.03.006View

Published Version

Abstract

arsine ocides

grignard reagents

heterocycles

organoarsines

ligands

The growing importance of triarylarsines as ligands for transition metal catalysis has sparked recent interest in new synthetic routes to tertiary arsines that avoid hazardous arsenous chloride reagents. However, safer methods for the synthesis of lesser explored arsine heterocycles, especially those containing As-C(sp(3)) bonds, remain lacking. We demonstrate for the first time that bench stable, less hazardous, arylarsine(III) oxides are effective substitutes for their corresponding chlorides in the one-pot construction of cyclic tertiary organoarsines from di-Grignard reagents. Several known and novel heterocycles have been prepared in reasonable yields, accommodating variations in both the diorganomagnesium reagent and electrophile, making this a modular approach to cyclic arsine assembly. (C) 2015 Elsevier By. All rights reserved.

Details

Title: Arsenous chloride-free synthesis of cyclic tertiary organoarsines from arylarsine oxides and di-Grignard reagents
Authors: Aaron M. Gregson (Author) - University of Wollongong
Steven M. Wales (Author) - University of Wollongong
Stephen J. Bailey (Author) - University of Wollongong
Paul A. Keller (Corresponding Author) - University of Wollongong
Publication details: Journal of Organometallic Chemistry, Vol.785, pp.77-83
Publisher: Elsevier BV
DOI: 10.1016/j.jorganchem.2015.03.006
ISSN: 1872-8561
Organisation Unit: Student Services and Engagement; School of Science, Technology and Engineering
Language: English
Record Identifier: 99707483802621
Output Type: Journal article

Metrics

19 Record Views

11 Times Cited - Web of Science

InCites Highlights

These are selected metrics from InCites Benchmarking & Analytics tool, related to this output

Web Of Science research areas: Chemistry, Inorganic & Nuclear; Chemistry, Organic

UN Sustainable Development Goals (SDGs)

This output has contributed to the advancement of the following goals:

Source: InCites