Boron trifluoride etherate functioning as a fluorine source in an iodosobenzene-mediated intramolecular aminofluorination of homoallylic amines

Jian Cui; Qun Jia; Ruo-Zhu Feng; Shan-Shan Liu; Tian He; Chi Zhang

doi:10.1021/ol500238k

Boron trifluoride etherate functioning as a fluorine source in an iodosobenzene-mediated intramolecular aminofluorination of homoallylic amines

Org Lett. 2014 Mar 7;16(5):1442-5. doi: 10.1021/ol500238k. Epub 2014 Feb 26.

Authors

Jian Cui¹, Qun Jia, Ruo-Zhu Feng, Shan-Shan Liu, Tian He, Chi Zhang

Affiliation

¹ State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), The Research Institute of Elemento-Organic Chemistry, Nankai University , Tianjin 300071, P. R. of China.

PMID: 24571373
DOI: 10.1021/ol500238k

Abstract

A widely used Lewis acid BF3·Et2O was shown to be capable of acting as an efficient fluorinating agent in an intramolecular aminofluorination reaction of homoallylic amines to provide 3-fluoropyrrolidines mediated by a commercially available hypervalent iodine(III) reagent PhIO at room temperature. A mechanism involving a carbocation intermediate was proposed on the basis of several experimental evidence.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amines / chemistry*
Boranes / chemistry*
Combinatorial Chemistry Techniques
Cyclization
Fluorine / chemistry*
Iodobenzenes / chemistry*
Lewis Acids / chemistry
Molecular Structure
Pyrrolidines / chemical synthesis*
Pyrrolidines / chemistry

Substances

Amines
Boranes
Iodobenzenes
Lewis Acids
Pyrrolidines
Fluorine
boron trifluoride etherate
iodosobenzene