Organic Chemistry Portal



A Highly Efficient Conversion of Primary or Secondary Alcohols into Fluorides with n-Perfluorobutanesulfonyl Fluoride-Tetrabutylammonium Triphenyldifluorosilicate

Xueqing Zhao*, Weiping Zhuang, Dongsheng Fang, Xiaowen Xue, Jingming Zhou

*Fujian Institute of Microbiology, Fuzhou 350007, P. R. of China, Email:

X. Zhao, W. Zhuang, D. Fang, X. Xue, J. Zhou, Synlett, 2009, 779-782.

DOI: 10.1055/s-0028-1087931

see article for more reactions


Direct fluorination of primary and secondary alcohols by a combination of perfluoro-1-butanesulfonyl fluoride (PBSF) and tetrabutylammonium triphenyldifluorosilicate (TBAT) under mild conditions provides the corresponding fluorides in high yields with inversion at the reaction center and suppressed elimination side reactions.

see article for more examples

Key Words

fluorination, elimination, nucleophilic substitution, stereoselectivity, PBSF, TBAT

ID: J60-Y2009-0850