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Synthesis 2009(22): 3897-3904  
DOI: 10.1055/s-0029-1217067
PSP
© Georg Thieme Verlag Stuttgart ˙ New York

Enol Phosphinates and Phosphonates: Practical Electrophiles for Cross-Coupling Strategies

Patrick G. Steel*a, Tom M. Woodsa,b
a Department of Chemistry, University of Durham, Science Laboratories, South Road Durham, DH1 3LE, UK
Fax: +44(191)3844737; e-Mail: p.g.steel@durham.ac.uk;
b Chemical Synthesis Laboratory, Swiss Federal Institute of Technology (EPFL), 1015 Lausanne, Switzerland
e-Mail: tom.m.woods@gmail.com;
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Publication History

Received 18 June 2009
Publication Date:
22 October 2009 (online)

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Abstract

Enol phosphinates and phosphonates can be readily prepared from simple lactams in high yields and are both stable and storable. Both these substrates can be employed successfully in homogeneous Suzuki-Miyaura and Stille cross-couplings protocols. Additionally, the phosphonate group can be immobilised on a phenol-on-polystyrene resin and utilised in a simple diversity linker strategy in which the coupled product is cleaved from the resin under Suzuki-Miyaura cross-coupling conditions.

Key words

lactams - arylboronic acids - stannanes - Suzuki-Miyaura coupling - Stille coupling - resin-bound enol phosphinate

16

In all cases, the 2-arylenamide products 6 are isolated as rotameric mixtures interconvertable at 60 ˚C as ascertained by simple VT NMR studies.