1446029-58-8Relevant articles and documents
Dehydrative Ring-Opening of gem-Difluorocyclopropyl Carbinols to Allylic Trifluoromethyl and Difluorohalomethyl Derivatives Promated by Titanium Tetrahalide
Ramasamy, Manickavasakam,Kuo, Sheng-Chu,Hsieh, Min-Tsang
, p. 5207 - 5210 (2020/08/12)
We report herein the titanium tetrahalide-promoted dehydrative ring-opening of gem-difluorocyclopropyl carbinols as a novel method for the synthesis of (E)-allylic CF3, (E)-allylic CF2Cl, and (E)-allylic CF2Br compounds. This TiF4-promoted reaction appears to proceed via a concerted SN2' mechanism. A control experiment revealed that the TiCl4-promoted ring-opening initially proceeds by conversion of the gem-difluorocyclopropyl carbinol into a gem-difluorocyclopropyl chloride intermediate.
Copper-catalyzed decarboxylative trifluoromethylation of allylic bromodifluoroacetates
Ambler, Brett R.,Altman, Ryan A.
supporting information, p. 5578 - 5581 (2013/11/19)
The development of new synthetic fluorination reactions has important implications in medicinal, agricultural, and materials chemistries. Given the prevalence and accessibility of alcohols, methods to convert alcohols to trifluoromethanes are desirable. However, this transformation typically requires four-step processes, specialty chemicals, and/or stoichiometric metals to access the trifluoromethyl-containing product. A two-step copper-catalyzed decarboxylative protocol for converting allylic alcohols to trifluoromethanes is reported. Preliminary mechanistic studies distinguish this reaction from previously reported Cu-mediated reactions.