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Rhodium-Catalyzed B-H Bond Insertion Reactions of Unstabilized Diazo Compounds Generated in Situ from Tosylhydrazones

Yue Pang, Qiao He, Zi-Qi Li, Ji-Min Yang, Jin-Han Yu, Shou-Fei Zhu*, Qi-Lin Zhou

*State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China, Email:

Y. Pang, Q. He, Z.-Q. Li, J.-M. Yang, J.-H. Yu, S.-F. Zhu, Q.-L. Zhou, J. Am. Chem. Soc., 2018, 140, 10663-10668.

DOI: 10.1021/jacs.8b05946


Rh-catalyzed B-H bond insertion of carbenes generated in situ from tosylhydrazones into stable borane adducts enables a promising method for organoborane synthesis. In addition, by using chiral dirhodium catalysts, an asymmetric version of the reaction with very good enantioselectivities was achieved. The products could be easily transformed into chiral alcohols and other widely used organoboron reagents with enantiomeric fidelity.

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Key Words

benzyl boranes

ID: J48-Y2018