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

Journal Article


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Abstract


  • 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(sp3) 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.

Publication Date


  • 2015

Citation


  • Gregson, A. M., Wales, S. M., Bailey, S. J. & Keller, P. A. (2015). Arsenous chloride-free synthesis of cyclic tertiary organoarsines from arylarsine oxides and di-Grignard reagents. Journal of Organometallic Chemistry, 785 77-83.

Scopus Eid


  • 2-s2.0-84925358935

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=3685&context=smhpapers

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/2664

Number Of Pages


  • 6

Start Page


  • 77

End Page


  • 83

Volume


  • 785

Abstract


  • 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(sp3) 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.

Publication Date


  • 2015

Citation


  • Gregson, A. M., Wales, S. M., Bailey, S. J. & Keller, P. A. (2015). Arsenous chloride-free synthesis of cyclic tertiary organoarsines from arylarsine oxides and di-Grignard reagents. Journal of Organometallic Chemistry, 785 77-83.

Scopus Eid


  • 2-s2.0-84925358935

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=3685&context=smhpapers

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/2664

Number Of Pages


  • 6

Start Page


  • 77

End Page


  • 83

Volume


  • 785