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Iron Porphyrin Catalyzed Insertion Reaction of N‑Tosylhydrazone-Derived Carbenes into X–H (X = Si, Sn, Ge) Bonds

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journal contribution
posted on 25.07.2018, 12:08 by En-Hui Wang, Yuan-Ji Ping, Zong-Rui Li, Hongling Qin, Zhen-Jiang Xu, Chi-Ming Che
An efficient Fe­(TPP)­Cl catalyzed insertion reaction of in situ generated benzylic carbenes from N-tosylhydrazones into X–H (X = Si, Sn, Ge) was developed. Silanes bearing tertiary, secondary, and primary (3°, 2°, and 1°) Si–H bonds all reacted well to afford insertion products in moderate to high yields (up to 97%), and the reaction time could be significantly shortened to 1 h under microwave irradiation. A programmable stepwise double insertion strategy was developed for the synthesis of unsymmetrical tetrasubstituted silanes.