An efficient approach for monofluorination via aqueous fluorolactonization reaction of 2,3-allenoic acids with selectfluor

Chao Zhou; Zhichao Ma; Zhenhua Gu; Chunling Fu; Shengming Ma

doi:10.1021/jo702409y

An efficient approach for monofluorination via aqueous fluorolactonization reaction of 2,3-allenoic acids with selectfluor

J Org Chem. 2008 Jan 18;73(2):772-4. doi: 10.1021/jo702409y. Epub 2007 Dec 23.

Authors

Chao Zhou¹, Zhichao Ma, Zhenhua Gu, Chunling Fu, Shengming Ma

Affiliation

¹ Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang, PR China.

PMID: 18154357
DOI: 10.1021/jo702409y

Abstract

We have developed a convenient method for the efficient monofluorination via the electrophilic fluorocyclization reaction of 2,3-allenoic acids with Selectfluor in MeCN in the presence of 10 equiv of H2O or even in pure water to afford beta-fluorobutenolides in moderate to high yields.

MeSH terms

Alkadienes / chemistry*
Carboxylic Acids / chemistry*
Cyclization
Diazonium Compounds / chemistry*
Fluorine / chemistry*
Hydrogen Bonding
Lactones / chemical synthesis*
Lactones / chemistry
Molecular Structure
Stereoisomerism
Water / chemistry

Substances

Alkadienes
Carboxylic Acids
Diazonium Compounds
Lactones
Water
Fluorine
selectfluor