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

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

Chem Commun (Camb). 2022 Oct 18;58(83):11705-11708. doi: 10.1039/d2cc01938h.

Authors

Michael M Wade Wolfe¹, Shuo Guo¹, Lucy S Yu¹, Trenton R Vogel¹, Joseph W Tucker², Nathaniel K Szymczak¹

Affiliations

¹ University of Michigan, 930 N. University Ave., Ann Arbor, MI, 48109, USA. nszym@umich.edu.
² Medicine Design, Pfizer Inc., Eastern Point Rd., Groton, CT, 06340, USA.

PMID: 36178029
DOI: 10.1039/d2cc01938h

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.

MeSH terms

Boron Compounds
Catalysis
Indicators and Reagents
Lewis Acids*

Substances

Boron Compounds
Indicators and Reagents
Lewis Acids
borazine