Efficient Cross-Coupling of Secondary Alkyltrifluoroborates with Aryl Chlorides - Reaction Discovery Using Parallel Microscale Experimentation
Spencer D. Dreher, Peter G. Dormer, Deidre L. Sandrock and Gary A. Molander*
*Department of Chemistry, University of Pennsylvania, 231
South 34th Street, Philadelphia, Pennsylvania 19104-6323, Email: gmolandr
sas.upenn.edu
S. D. Dreher, P. G. Dormer, D. L. Sandrock, G. A. Molander, J. Am. Chem. Soc., 2008, 130, 9257-9259.
DOI: 10.1021/ja8031423
see article for more reactions
Abstract
Microscale parallel experimentation was used to discover catalyst systems capable of coupling secondary organotrifluoroborates with aryl chlorides and bromides. A ligand-dependent β-hydride elimination/reinsertion mechanism was implicated in the cross-coupling of more hindered substrates, leading to isomeric mixtures of coupled products in some cases.
see article for more examples
Suzuki-Miyaura Cross-Coupling Reactions of Primary Alkyltrifluoroborates with Aryl Chlorides
S. D. Dreher, S.-E. Lim, D. L. Sandrock, G. A. Molander, J. Org. Chem., 2009, 74, 3626-3631.
Cross-Coupling of Cyclopropyl- and Cyclobutyltrifluoroborates with Aryl and Heteroaryl Chlorides
G. A. Molander, P. E. Gormisky, J. Org. Chem., 2008, 73, 7481-7485.
Key Words
ID: J48-Y2008-1970
