Nucleophilic strategies to construct –CF2– linkages using borazine-CF2Ar reagents

Michael M. Wade Wolfe; Shuo Guo; Lucy S. Yu; Trenton R. Vogel; Joseph W. Tucker; Nathaniel K. Szymczak

doi:10.1039/D2CC01938H

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Nucleophilic strategies to construct –CF₂– linkages using borazine-CF₂Ar reagents†

Michael M. Wade Wolfe,^a Shuo Guo,^a Lucy S. Yu,^a Trenton R. Vogel,^a Joseph W. Tucker^b and Nathaniel K. Szymczak

*^a

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* Corresponding authors

^a University of Michigan, 930 N. University Ave., Ann Arbor, MI, USA
E-mail: nszym@umich.edu

^b Medicine Design, Pfizer Inc., Eastern Point Rd., Groton, CT, USA

Abstract

Using a Lewis acid-quenched CF₂Ph⁻ reagent, we show C–C bond formation through nucleophilic addition reactions to prepare molecules containing internal –CF₂– linkages. We demonstrate C(sp²)–C(sp³) coupling using both S_NAr reactions and Pd-catalysis. Finally, C(sp³)–C(sp³) bonds are forged using operationally simple S_N2 reactions that tolerate medicinally-relevant motifs.

This article is part of the themed collection: Boron Chemistry in the 21st Century: From Synthetic Curiosities to Functional Molecules

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Article information

DOI: https://doi.org/10.1039/D2CC01938H
Article type: Communication
Submitted: 04 Apr 2022
Accepted: 21 Sep 2022
First published: 30 Sep 2022

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Chem. Commun., 2022,58, 11705-11708

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Nucleophilic strategies to construct –CF₂– linkages using borazine-CF₂Ar reagents

M. M. Wade Wolfe, S. Guo, L. S. Yu, T. R. Vogel, J. W. Tucker and N. K. Szymczak, Chem. Commun., 2022, 58, 11705 DOI: 10.1039/D2CC01938H

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