Work

Fe(III)/NaBH 4 -Mediated Free Radical Hydrofluorination of Unactivated Alkenes

Year: 2012

Type: article

Abstract: A powerful Fe(III)/NaBH(4)-mediated free radical hydrofluorination of unactivated alkenes is disclosed using Selectfluor reagent as a source of fluorine and resulting in exclusive Markovnikov addition. In contrast to the traditional and unmanageable free radical hydrofluorination of alkenes, the Fe(III)/NaBH(4)-mediated reaction is conducted under exceptionally mild reaction conditions (0 °C, 5 min, CH(3)CN/H(2)O). The reaction can be conducted open to the air and with water as a cosolvent and demonstrates an outstanding substrate scope and functional group tolerance.

Source: Journal of the American Chemical Society

DOI: 10.1021/ja3063716

Authors: Timothy J. Barker, Dale L. Boger

Institution: Scripps Research Institute

Language: English

Topic: Fluorine in Organic Chemistry

Subfield: Pharmaceutical Science

Field: Pharmacology, Toxicology and Pharmaceutics

Domain: Life Sciences

Open Access status: green

Funders: National Institutes of Health, National Cancer Institute