Eberly College of Arts and Sciences
Gold-catalyzed C-heteroatom (C-X) coupling reactions are evaluated without using sacrificial oxidants. Vital to the success of this methodology is the nucleophile-assisted activation of aryldiazonium salts, which could be an effective oxidant to convert Au(I) to Au(III) even without the addition of assisting ligand or photocatalyst. By accelerating reaction kinetics to outcompete C-C homo-coupling or diazonium dediazoniation, gold-catalyzed Sandmeyer reactions were achieved with different nucleophiles, forming C-Br, C-S and C-P bonds in high yields and selectivity.
Digital Commons Citation
Peng, Haihui; Cai, Rong; Xu, Chang; Chen, Hao; and Shi, Xiaodong, "Nucleophile Promoted Gold Redox Catalysis with diazonium: CBr, C-S and C-P Bond Formation through Catalytic Sandmeyer Coupling" (2016). Faculty & Staff Scholarship. 2364.
Peng, H., Cai, R., Xu, C., Chen, H., & Shi, X. (2016). Nucleophile promoted gold redox catalysis with diazonium salts: C–Br, C–S and C–P bond formation through catalytic Sandmeyer coupling. Chemical Science, 7(9), 6190–6196. https://doi.org/10.1039/c6sc01742h