Copper-Catalyzed Benzylic C-H Bond Thiocyanation: Enabling Late Stage Diversifications

The rapid growth of using C-H bond as cross-coupling partners is reshaping the landscape of organic synthesis. C(sp(3))-H functionalization via hydrogen atom transfer (HAT) represents the most compelling strategy in this avenue. Here, we demonstrate an efficient method for benzylic C-H bond thiocyanation via copper-catalyzed radical relay. The reaction exhibits broad substrate scope and exquisite benzylic selectivity with C-H substrates as limiting reagents. In addition, the benzyl thiocyanates are readily converted to other pharmaceutically important motifs, including isothiocyanate, thiourea, and others, highlighting the broad utility of this method. [GRAPHICS] .

Automated summary

The rapid growth of using C-H bond as cross-coupling partners has been reshaping the landscape of organic synthesis. The efficient method for benzylic C-H bond thiocyanation via copper-catalyzed radical relay demonstrates broad substrate scope and exquisite selectivity, with easy conversion to other pharmaceutically important motifs. This highlights the broad utility of this method.