Borane-Mediated Highly Secondary Selective Deoxyfluorination of Alcohols.

ABSTRACT: Organofluorine compounds are vital across multiple sectors, hence highly selective methods to install fluorine are of considerable importance. The deoxyfluorination of alcohols is a key approach to prepare organofluorine compounds, however, a highly secondary (2°)-selective deoxyfluorination of alcohols has not been realized to date. Herein, we report that borane-mediated deoxyfluorination results in high 2°-selectivity in inter- and intra-molecular competition reactions versus primary (1°), tertiary (3°) and even benzylic (Bn) alcohols. This is an operationally simple method using only commercial reagents (e.g., Et₃N ⋅ 3HF) that starts from the alcohol which is converted to the O-alkyl-N-H-isourea in situ. The origin of the high 2°-selectivity was elucidated to be due to the re

SUBMITTER: Willcox DR 

PROVIDER: S-EPMC11795720 | biostudies-literature | 2025 Feb

REPOSITORIES: biostudies-literature