Synthesis 2013; 45(2): 265-271
DOI: 10.1055/s-0032-1316825
paper
© Georg Thieme Verlag Stuttgart · New York

Efficient Multigram Syntheses of Air-Stable, Chiral Primary Phosphine Ligand Precursors via Palladium-Catalyzed Phosphonylation of Aryltriflates

Arne Ficks
School of Chemistry, Bedson Building, Newcastle University, Newcastle upon Tyne, NE1 7RU, UK   Fax: +44(191)2226929   Email: lee.higham@ncl.ac.uk
,
Connor Sibbald
School of Chemistry, Bedson Building, Newcastle University, Newcastle upon Tyne, NE1 7RU, UK   Fax: +44(191)2226929   Email: lee.higham@ncl.ac.uk
,
Stephen Ojo
School of Chemistry, Bedson Building, Newcastle University, Newcastle upon Tyne, NE1 7RU, UK   Fax: +44(191)2226929   Email: lee.higham@ncl.ac.uk
,
Ross W. Harrington
School of Chemistry, Bedson Building, Newcastle University, Newcastle upon Tyne, NE1 7RU, UK   Fax: +44(191)2226929   Email: lee.higham@ncl.ac.uk
,
William Clegg
School of Chemistry, Bedson Building, Newcastle University, Newcastle upon Tyne, NE1 7RU, UK   Fax: +44(191)2226929   Email: lee.higham@ncl.ac.uk
,
Lee J. Higham*
School of Chemistry, Bedson Building, Newcastle University, Newcastle upon Tyne, NE1 7RU, UK   Fax: +44(191)2226929   Email: lee.higham@ncl.ac.uk
› Author Affiliations
Further Information

Publication History

Received: 25 September 2012

Accepted after revision: 14 November 2012

Publication Date:
13 December 2012 (online)


Abstract

Air-stable, chiral primary phosphines have been synthesized on a multigram scale. The key synthetic step is an optimized palladium-catalyzed phosphonylation reaction of aryltriflates, which opens up a valuable synthetic route to a chiral scaffold that is easily derivatized into novel phosphines.