Ligand-Enabled Copper-Catalyzed Regio- and Stereoselective Allylboration of 1-Trifluoromethylalkenes

A copper-catalyzed regio-and stereoselective allylboration of 1-trifluoromethylalkenes with bis(pinacolato)-diboron (pinB-Bpin) and allylic chlorides has been developed to form functionalized trifluoromethylated products with high diastereoselectivity. The key to success is the judicious choice of Cs2CO3 base and t-Bu-modified dppe-type ligand, which enables the otherwise challenging high catalyst turnover and suppression of the competing defluorination side reaction from an alkylcopper intermediate. The product derivatization of the resulting Bpin moiety can deliver diverse CF3-containing molecules with high stereochemical fidelity.

Automated summary

A copper-catalyzed regio- and stereoselective allylboration reaction has been developed to functionalize 1-trifluoromethylalkenes with bis(pinacolato)diboron and allylic chlorides, resulting in high diastereoselective trifluoromethylated products. The success of this reaction relies on the careful selection of Cs2CO3 base and t-Bu-modified dppe-type ligand, which allows for efficient catalyst turnover and suppression of defluorination side reactions. The resulting Bpin moiety can be derivatized to provide diverse CF3-containing molecules with high stereochemical fidelity.