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Raising the pKa Limit of "Soft" Nucleophiles in Palladium-Catalyzed Allylic Substitutions: Application of Diarylmethane Pronucleophiles

Sheng-Chun Sha, Jiadi Zhang, Patrick J. Carroll and Patrick J. Walsh*

*Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States, Email: pwalshsas.upenn.edu

S.-C. Sha, J. Zhang, P. J. Carroll, P. J. Walsh, J. Am. Chem. Soc., 2013, 135, 17602-17609.

DOI: 10.1021/ja409511n (free Supporting Information)



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Abstract

A room temperature Pd-catalyzed allylic substitution of a wide range of soft nucleophiles derived from diarylmethane provides rapid access to the corresponding allylated products. A procedure for Pd-catalyzed allylic substitutions to afford diallylation products with quaternary centers is also described.

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Key Words

Tsuji-Trost reaction, allylation, benzylation


ID: J48-Y2013