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: gmolandrsas.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 (free Supporting Information)
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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.
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S. D. Dreher, S.-E. Lim, D. L. Sandrock, G. A. Molander, J. Org. Chem., 2009, 74, 3626-3631.
G. A. Molander, P. E. Gormisky, J. Org. Chem., 2008, 73, 7481-7485.