Lewis acid / Base-free Strategy for the Synthesis of 2-Arylthio and Selenyl Benzothiazole / Thiazole and Imidazole

Abstract

A Cu(II)-catalyzed Csp2-Se and Csp2-Sulfur bond formation was achieved with moderate to good yields without the aid of Lewis acid and base. The reaction is compatible with a wide range of heterocycles such as benzothiazole, thiazole, and imidazole. Also, this typical protocol is found to be active in thio-selenation via S-H activation. Additionally, we proposed a plausible mechanistic pathway involving Cu(III) putative intermediate.

Transition-Metal-Catalyzed C–S, C–Se, and C–Te Bond Formations via Cross-Coupling and Atom-Economic Addition Reactions. Achievements and Challenges

“…The Cu­(OAc) 2 -catalyzed reaction of “acidic” azoles with diphenyl disulfides and diphenyl diselenides proceeds with good results without a base and ligands (Scheme , C) . According to the proposed mechanism, disproportionation of Cu­(II) results in the formation of Cu­(III) (Scheme , D).…”

Ni-catalyzed unnatural prenylation and cyclic monoterpenation of heteroarenes with isoprene

“…Nitrogen containing cyclic compounds widely exist in various natural products and pharmaceutical molecules. The catalytic C-H functionalization of heterocycles [52][53][54][55][56][57][58][59][60][61][62][63][64][65][66][67][68][69][70] is a straightforward and economic route to achieve post-modification of drugs and active molecules. And the introduction of dimethylallyl-related units (C5 skeletons) [71][72][73][74][75][76][77][78][79][80][81][82][83][84][85][86][87][88] into functional molecules often leads to dramatic changes in their lipophilicities and metabolic stabilities.…”