Fluorinating agents diethylaminosulfur trifluoride

Dialkylaminosulfur trifluorides, - exemplified by diethylaminosulfur trifluoride (Et2NSF3, DAST), were introduced into carbohydrate chemistry as fluorinating agents by Sharma and Korytnyk, and they can be... 

A comparison of various fluorinating agents in the preparation of fluoride 13, i.e. (2-chloro-1,1,2-trifluoroethyl)diethylamine and diethylaminosulfur trifluoride (R = H), tetrafluoro(phen-yl)-A5-phosphane (R = TMS), and potassium fluoride (R = Ts), has shown that the highest stereoselectivity is achieved with potassium fluoride and (2-chloro-l,1,2-trifluoroethyl)-diethylamine.19 The fluorination with tctrafluoro(phenyl)-7.5-phosphane proceeds, at least in part, via a carbocation and with a relatively low enantioselectivity.15... 

M. G. Straatmann and M. J. Welch, Fluorine-18-Iabeled diethylaminosulfur trifluoride (DAST) A fluorine-for-hydroxyl fluorinating agent, J. Nucl. Med. 78 151 (1977). 

Diethylaminosulfur trifluoride (DAST) has become one of the most important fluorinating agents (75JOC574,75JOU72 76JOU973 870R513). It is mainly used to transform alcohols, aldehydes, or ketones into mono-or difluorinated compounds. It has been used successfully in sugar, nucleo-... 

Diethylaminosulfur trifluoride (DAST. 1), an established fluorinating agent, was first synthesized in 1970 from (diethylamino)triinethylsilane and sulfur tetrafluoride. ... 

Fluorinated compounds exhibit an enhanced metabolic stability and are therefore valuable compounds in the pharmaceutical chemistry. Dialkylaminosulfur trifluoride derivatives (Figure 6.1) are common commercially available nucleophilic fluorinating agents, but are thermally instable and need careful handling. Therefore, reactions vith diethylaminosulfur trifluoride (DAST, 1) or bis(methox-yethyl)aminosulfur trifluoride (Deoxo-Fluor , 2) are suitable for processing in microfluidic devices. 

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