Construction of trifluoromethyl-containing heterocycles from trifluoroacetimidoyl chlorides and derivatives

Abstract

Recent advances in the direct synthesis of trifluoromethyl-containing heterocycles from trifluoroacetimidoyl chlorides (TFAICs) and derivatives, including trifluoroacetimidohydrazides (TFAIHs) and CF3-imidoyl sulfoxonium ylides (TFISYs), are systematically summarized and discussed. The cascade...

Multiple-cycle photochemical cascade reactions

“…Moreover, it can substantially modify the lipid solubility and biological activities of the parent compounds. 24,25 Given these unique properties, the development of trifluoromethylation reagents and reactions has been a critical area of research in organic and medicinal chemistry for nearly five decades. 26,27 In 2014, the group of Cho reported a photocatalyzed hydro-trifluoromethylation of terminal alkynes 1 using trifluoromethyl iodide 2 as the trifluoromethylating reagent.…”

Synthesis of 2‐Trifluoromethyl‐4‐aminoquinolines via Heating‐Promoted Multi‐component Reaction of CF3‐Imidoyl Sulfoxonium Ylides and Amines with Difluorocarbene as a C1 Synthon†

“…It is found that TFISYs could be applied as 1‐, 3‐ or 5‐atom synthons to build structurally diversified CF 3 ‐containing heterocycles. Inspired by the good applicability of highly reactive PDFA and our continuous effort on the efficient synthesis of trifluoromethyl‐substituted heterocycles, [ 15 ] we wish to merge TFISYs with PDFA to establish a more general and practical approach for the construction of 2‐trifluoromethyl quinolines. Herein, we report our recent findings about multi‐component reaction of TFISYs and amines with PDFA as a C1 synthon in the presence or absence of elemental sulfur under simple heating conditions (Scheme 1d).…”

Copper-Mediated Cyclization of Terminal Alkynes with CF3-Imidoyl Sulfoxonium Ylides To Construct 5-Trifluoromethylpyrroles

“…Due to the high lipophilicity, metabolic stability, and binding selectivity of the trifluoromethyl group, the introduction of it onto the pyrrole skeleton greatly alters the physicochemical properties and promotes the applications (several examples in Figure ). At present, the strategies for the construction of CF 3 -pyrroles can be divided into two main categories including trifluoromethylation of pyrroles by trifluoromethyl reagents and cyclization of CF 3 -containing building blocks . Compared with the latter, direct trifluoromethylation often suffers from the puzzle of regioselectivity and requires preprepared pyrroles as the starting materials.…”