Iron Porphyrin Catalyzed Insertion Reaction of N-Tosylhydrazone-Derived Carbenes into X-H (X = Si, Sn, Ge) Bonds.
En-Hui WangYuan-Ji PingZong-Rui LiHongling QinZhen-Jiang XuChi-Ming ChePublished in: Organic letters (2018)
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.