2021 · ORGANIC LETTERS

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

Lefebvre, Gauthier, Charron, Olivier, Cossy, Janine, Meyer, Christophe

Journal
ORGANIC LETTERS
Année
2021
Volume
23
Numéro
14
Pages
5491-5495
Mois
JUL 16
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.

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