Synthesis of Chiral α-CF₃-Substituted Benzhydryls via Cross-Coupling Reaction of Aryltitanates

Andrii Varenikov, Evgeny Shapiro and Mark Gandelman*

*Schulich Faculty of Chemistry, Technion - Israel Institute of Technology, Technion City, Haifa 3200008, Israel, Email: chmarktechnion.ac.il

A. Varenikov, E. Shapiro, M. Gandelman, Org. Lett., 2020, 22, 9386-9391.

DOI: 10.1021/acs.orglett.0c03673

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Abstract

A nickel-catalyzed enantioselective cross-coupling reaction of aryl titanates with α-CF₃-benzyl bromides enables the synthesis of chiral α-CF₃-substituted benzhydryls in good yields and excellent enantioselectivities. The use of commercially available anesthetic halothane as a cheap fluorinated building block in a sequential one-pot reaction with two different aryl titanates is also described.

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Key Words

arylation, benzylic trifluoromethanes

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ID: J54-Y2020