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Suzuki-Miyaura Cross-Coupling Reactions of Primary Alkyltrifluoroborates with Aryl Chlorides

Spencer D. Dreher, Siang-Ee Lim, 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, S.-E. Lim, D. L. Sandrock, G. A. Molander, J. Org. Chem., 2009, 74, 3626-3631.

DOI: 10.1021/jo900152n (free Supporting Information)


Abstract

Parallel microscale experimentation was used to develop general conditions for the Suzuki-Miyaura cross-coupling of diversely functionalized primary alkyltrifluoroborates with a variety of aryl chlorides. The conditions that were previously identified to promote the cross-coupling of secondary alkyltrifluoroborates with aryl chlorides were not optimal for primary alkyltrifluoroborates.

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Efficient Cross-Coupling of Secondary Alkyltrifluoroborates with Aryl Chlorides - Reaction Discovery Using Parallel Microscale Experimentation

S. D. Dreher, P. G. Dormer, D. L. Sandrock, G. A. Molander, J. Am. Chem. Soc., 2008, 130, 9257-9259.


Key Words

Suzuki Coupling, Arenes


ID: J42-Y2009-1450