2521. Copper(I) Thiophene-2-carboxylate

Nomenclature

CAS number: 68986-76-5
(2-Thiophenecarboxylato-κO2,κS1)copper; CuTC.
C5H3CuO2S; mol wt 190.69.
C 31.49%, H 1.59%, Cu 33.32%, O 16.78%, S 16.82%.

Description and references

Copper(I) reagent; promotes modified Stille cross-coupling reactions and Ullman-type couplings. Prepn: G. D. Allred, L. S. Liebeskind, J. Am. Chem. Soc. 118, 2748 (1996). Synthetic applications: S. Zhang et al., J. Org. Chem. 62, 2312 (1997); I. Paterson, J. Man, Tetrahedron Lett. 38, 695 (1997); C. Savarin et al., Org. Lett. 3, 91, 2149 (2001); G. Borsato et al., J. Org. Chem. 67, 7894 (2002); M. d'Augustin et al., Angew. Chem. Int. Ed. 44, 1376 (2005). Brief review: A. Innitzer, Synlett 2005, 2405-2406.

Chemical structure

Properties

Tan, air-stable, non-hygroscopic powder.

Use

Mediator in intermolecular cross-coupling reactions, asymmetric 1,4-additions, and allylation reactions.