Direct Vicinal Difunctionalization of Alkynes: An Efficient Approach Towards the Synthesis of Highly Functionalized Fluorinated Alkenes

Abstract

International audienc

Photoredox‐Catalyzed Stereoselective Conversion of Alkynes into Tetrasubstituted Trifluoromethylated Alkenes

“…[3] Step-economic and versatile stereoselective synthetic methods towards tetrasubstituted trifluoromethylated alkenes,h owever,h ave been extremely limited thus far. [5,6] Herein, we describe an ovel stereoselective Scheme 1. Konno et al developed methods based on the carbometalation of CF 3 -substituted alkynes (Scheme 1b).…”

Copper-Catalyzed Trifluoromethylation of Alkoxypyridine Derivatives

“…This effect is more pronounced when a trifluoromethyl group is introduced, evidenced by the surge in the number of FDA-approved CF 3 -group containing drugs in recent years [ 7 , 8 , 9 ]. There are multiple approaches for the establishment of the trifluoromethyl group, including nucleophilic, radical, and electrophilic routes [ 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 ]. Our objective was to systematically study the copper-catalyzed trifluoromethylation [ 24 ] of alkoxypyridine derivatives and their benzologs that could serve as useful building blocks in medicinal chemistry.…”

Stereoselective cobalt-catalyzed halofluoroalkylation of alkynes

“… 1 Fluoroalkylation methods of easily accessible precursors have therefore attracted great interest in the past years. 2 , 3 While many protocols are substitution processes that require highly pre-functionalized starting materials and produce unwanted by-products, direct additions to unsaturated hydrocarbons exhibit higher modularity and atom-efficiency and provide ample opportunities of regio- and stereocontrol. The addition of halo-fluoroalkanes to alkynes is an especially attractive tool due to the easy availability of the reagents and the great synthetic versatility of the resultant halo-fluoroalkenes.…”