B-alkyl suzuki-miyaura cross-coupling reactions with air-stable potassium alkyltrifluoroborates

Gary A Molander; Chang-Soo Yun; María Ribagorda; Betina Biolatto

doi:10.1021/jo0343331

B-alkyl suzuki-miyaura cross-coupling reactions with air-stable potassium alkyltrifluoroborates

J Org Chem. 2003 Jul 11;68(14):5534-9. doi: 10.1021/jo0343331.

Authors

Gary A Molander¹, Chang-Soo Yun, María Ribagorda, Betina Biolatto

Affiliation

¹ Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA. gmolandr@sas.upenn.edu

PMID: 12839444
DOI: 10.1021/jo0343331

Abstract

The palladium-catalyzed cross-coupling reaction of substituted potassium alkyltrifluoroborates with aryl halides and aryl triflates proceeds readily with moderate to good yields. The potassium alkyltrifluoroborates 1, 2, and 3a-e were easily synthesized and obtained as air-stable crystalline solids that can be stored for long periods of time. All of the cross-couplings proceed under the same reaction conditions using PdCl(2)(dppf).CH(2)Cl(2) as catalyst in THF-H(2)O in the presence of 3 equiv of Cs(2)CO(3) as base.