DAST

CAS 38078-09-0, Cat. No EN300-97056

Reagent for deoxofluorination

DAST is a reagent for deoxofluorination that is still actual in organic synthesis. It is a yellow liquid that is relatively safe compared to SF₄ but requires careful working. DAST can convert alcohols to fluorides aldehydes and unhindered ketones to difluorides and finally carboxylic acids to acyl fluoride, and sulfoxides to α-fluoro sulfides with high yields. In some cases, DAST can promote cationic rearrangements (Wagner-Meerwein rearrangement, pinacol rearrangement) which is important to remember.

Synonyms: diethylaminosulfur trifluoride, Sulfur, (N-ethylethanaminato)trifluoro-, (T-4)-, Ethanamine, N-ethyl-, sulfur complex, (T-4), (N-Ethylethanaminato)trifluorosulfur, trifluoro(diethylamino)sulfur, (Diethylamino)sulfur trifluoride

Selected publication

1. Diethylaminosulfurtrifluoride.

Fauq A. H.; Singh R. P.; Meshri D. T. Encyclopedia of Reagents for Organic Synthesis 2006. DOI: 10.1002/047084289X.rd175

2. Achievements in Fluorination Using Variable Reagents through a Deoxyfluorination Reaction.

Aggarwal T.; Sushmita; Verma A. K. Organic Chemistry Frontiers 2021, 8 (22), 6452–6468. DOI: 10.1039/D1QO00952D

3. Enantiospecific Deoxyfluorination of Cyclic α-OH-β-Ketoesters.

Mairhofer C.; Haider V.; Bögl T.; Waser M. Org Biomol Chem 2021, 19 (1), 162–165. DOI: 10.1039/D0OB02152K