Copper-promoted/copper-catalyzed trifluoromethylselenolation reactions

Abstract

Copper catalysis and, more generally, copper chemistry are pivotal for modern organofluorine chemistry. Major advances have been made in the field of trifluoromethylselenolations of organic compounds where copper catalysis played a crucial role. Recent developments in this field are highlighted in this minireview.

Keywords: copper catalysis; fluorine; homogenous catalysis; trifluoromethylselenolation.

Scheme 1

Process for the formation of C(sp³)–SeCF₃ bonds with [(bpy)CuSeCF₃]₂ developed by the group of Weng.

Scheme 2

Trifluoromethylselenolation of vinyl and (hetero)aryl halides with [(bpy)CuSeCF₃]₂ by the group of Weng.

Scheme 3

Trifluoromethylselenolation of terminal alkynes using [(bpy)CuSeCF₃]₂ by the group of You and Weng.

Scheme 4

Trifluoromethylselenolation of carbonyl compounds with [(bpy)CuSeCF₃]₂ by the group of Weng.

Scheme 5

Trifluoromethylselenolation of α,β-unsaturated ketones with [(bpy)CuSeCF₃]₂ by the group of Weng.

Scheme 6

Trifluoromethylselenolation of acid chlorides with [(bpy)CuSeCF₃]₂ by the group of Weng.

Scheme 7

Synthesis of 2-trifluoromethylselenylated benzofused heterocycles with [(bpy)CuSeCF₃]₂ by the group of Weng.

Scheme 8

Difunctionalization of terminal alkenes and alkynes with [(bpy)CuSeCF₃]₂ by the group of Liang.

Scheme 9

Synthesis of Me₄NSeCF₃.

Scheme 10

Oxidative trifluoromethylselenolation of terminal alkynes and boronic acid derivatives with Me₄NSeCF₃ by the group of Rueping.

Scheme 11

Trifluoromethylselenolation of diazoacetates and diazonium salts with Me₄NSeCF₃ by the group of Goossen.

Scheme 12

Trifluoromethylselenolation with ClSeCF₃ by the group of Tlili and Billard.

Scheme 13

Trifluoromethylselenolation with TsSeCF₃ by the group of Tlili and Billard.

Scheme 14

Copper-catalyzed synthesis of a selenylated analog 30 of Pretomanid developed by the group of Tlili and researchers from Novartis.

Scheme 15

One-pot procedures for C–SeCF₃ bond formations developed by Hor and Weng, Deng and Xiao, and Rueping.