In situ ortho-lithiation/functionalization of pentafluorosulfanyl arenes

Autor:	Thanh V. Le, Olafs Daugulis
Rok vydání:	2022
Předmět:	Materials Chemistry Metals and Alloys Ceramics and Composites General Chemistry Article Catalysis Surfaces Coatings and Films Electronic Optical and Magnetic Materials
Zdroj:	Chem Commun (Camb)
ISSN:	1364-548X 1359-7345
DOI:	10.1039/d1cc06140b
Popis:	A general method for ortho-functionalization of pentafluorosulfanyl arenes has been developed. ortho-Lithiation with lithium tetramethylpiperidide at −60 °C in the presence of silicon, germanium, and tin electrophiles affords trapped products in moderate to high yields. Precise temperature regimes and the presence of electrophiles during lithiation are important for successful reactions, since the pentafluorosulfanyl group acts as a competent leaving group at temperatures above −40 °C. Fluoro, bromo, iodo, enolizable keto, cyano, ester, amide, and unsubstituted amino functionalities are compatible with the reaction conditions. Conversion of 2-dimethylsilylpentafluorosulfanyl benzene to 2-halosubstituted derivatives, useful as starting materials in cross-coupling chemistry, was also demonstrated.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::d88349cb9e3739b7d3a2b06e2a01d44a https://doi.org/10.1039/d1cc06140b Zobrazit plný text záznamu