Organic Chemistry Portal

Abstracts

Search:

Suzuki-Miyaura Cross-Coupling of Potassium Trifluoroboratohomoenolates

Gary A. Molander and Daniel E. Petrillo

*Roy and Diana A. Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, Email: gmolandrsas.upenn.edu

G. A. Molander, D. E. Petrillo, Org. Lett., 2008, 10, 1795-1798.

DOI: 10.1021/ol800357c (free Supporting Information)


Abstract

Ketone-, ester-, and amide-containing potassium trifluoroboratohomoenolates were prepared in good yields from the corresponding unsaturated carbonyl compounds. They are effective coupling partners in the Suzuki-Miyaura reaction with various electrophiles including electron-rich and electron-poor aryl bromides and -chlorides.

see article for more examples



Single-Electron Transmetalation: Photoredox/Nickel Dual Catalytic Cross-Coupling of Secondary Alkyl β-Trifluoroboratoketones and -esters with Aryl Bromides

J. C. Tellis, J. Amani, G. A. Molander, Org. Lett., 2016, 18, 2994-2997.

Copper-Catalyzed β-Boration of α,β-Unsaturated Carbonyl Compounds with Tetrahydroxydiborane

G. A. Molander, S. A. McKee, Org. Lett., 2011, 13, 4648-4687.


Key Words

Suzuki Coupling, Arylation, Alkyltrifluoroborates


ID: J54-Y2008-1200