Work

In situ ortho -lithiation/functionalization of pentafluorosulfanyl arenes

Year: 2021

Type: article

Abstract: -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.

Source: Chemical Communications

DOI: 10.1039/d1cc06140b

Authors: Thanh V. Le, Olafs Daugulis

Institution: University of Houston

Language: English

Topic: Fluorine in Organic Chemistry

Subfield: Pharmaceutical Science

Field: Pharmacology, Toxicology and Pharmaceutics

Domain: Life Sciences

Open Access status: green

Funders: Welch Foundation, National Institute of General Medical Sciences

Awards: G2854228422, New Methods for Direct Carbon-Hydrogen Bond Functionalization