Frustrated Lewis pair catalyzed hydrosilylation and hydrosilane mediated hydrogenation of fulvenes

Sergej Tamke, Constantin-G. Daniliuc, Jan Paradies
2014 Organic and biomolecular chemistry  
The frustrated Lewis pair (FLP) mediated hydrosilylation of pentafulvenes is described yielding allyl silanes with high regioselectivity in excellent yields. While phenyl substituted allyl silanes undergo B(C 6 F 5 ) 3mediated rearrangement to vinyl silanes, dimethyl derivatives experience FLP-catalyzed hydrogenation followed by an unprecedented protodesilylation. This observation allowed the metal-free hydrogenation of 6,6-dimethylfulvene to iso-propyl cyclopentene according to a FLP-catalyzed
more » ... to a FLP-catalyzed triple domino reaction consisting of hydrosilylation, hydrogenation and protodesilylation. The mechanisms were investigated by deuteration experiments. † Electronic supplementary information (ESI) available: General information; synthetic procedures; NMR spectroscopic data. CCDC 1008790. For ESI and crystallographic data in CIF or other electronic format see
doi:10.1039/c4ob01346h pmid:25293817 fatcat:yrokhfbqsjdrfcf7ggrdn6lbsq