Radical Addition of SF5Cl to Cyclopropenes: Synthesis of (Pentafluorosulfanyl)cyclopropanes

Gauthier Lefebvre; Olivier Charron; Janine Cossy; Christophe Meyer

doi:10.1021/acs.orglett.1c01840

Radical Addition of SF₅Cl to Cyclopropenes: Synthesis of (Pentafluorosulfanyl)cyclopropanes

Org Lett. 2021 Jul 16;23(14):5491-5495. doi: 10.1021/acs.orglett.1c01840. Epub 2021 Jun 25.

Authors

Gauthier Lefebvre¹, Olivier Charron¹, Janine Cossy¹, Christophe Meyer¹

Affiliation

¹ Molecular, Macromolecular Chemistry, and Materials, ESPCI Paris-PSL, CNRS, 10 rue Vauquelin, 75005 Paris, France.

PMID: 34170712
DOI: 10.1021/acs.orglett.1c01840

Abstract

With the goal of accessing yet unknown SF₅-cyclopropyl building blocks, the radical addition of SF₅Cl to cyclopropenes was investigated. Addition of the SF₅ radical occurs regioselectively at the less substituted carbon of cyclopropenes and trans to the most hindered substituent at C3, while chlorine atom transfer proceeds with moderate to high levels of diastereocontrol. The carbon-chlorine bond in the resulting adducts can undergo subsequent radical reduction or be involved in a radical cyclization.