TY - JOUR
T1 - Facile access to silyl-functionalized N-heterocyclic olefins with HSiCl3
AU - Ghadwal, Rajendra S.
AU - Reichmann, Sven O.
AU - Engelhardt, Felix
AU - Andrada, Diego M.
AU - Frenking, Gernot
PY - 2013/9/19
Y1 - 2013/9/19
N2 - N-heterocyclic olefins (NHOs), IPrCH2 (1) and SIPrCH2 (2) (IPrCH2 = (N(2,6-iPr2C6H3)CH)2CCH2 and SIPrCH2 = (N(2,6-iPr2C6H3)CH2)2CCH2), react with HSiCl3 and afford IPrCH(SiHCl2) (3) and SIPrCH(SiHCl2) (4), respectively. Compounds 3 and 4 have been isolated in almost quantitative yield. Interestingly, treatment of the silylene IPr±SiCl2 with 1 also affords 3, where silylene insertion into a C-H bond is observed. Computational analysis shows a high energy barrier for silylene insertion, therefore a protonation-deprotonation mechanism is more likely.
AB - N-heterocyclic olefins (NHOs), IPrCH2 (1) and SIPrCH2 (2) (IPrCH2 = (N(2,6-iPr2C6H3)CH)2CCH2 and SIPrCH2 = (N(2,6-iPr2C6H3)CH2)2CCH2), react with HSiCl3 and afford IPrCH(SiHCl2) (3) and SIPrCH(SiHCl2) (4), respectively. Compounds 3 and 4 have been isolated in almost quantitative yield. Interestingly, treatment of the silylene IPr±SiCl2 with 1 also affords 3, where silylene insertion into a C-H bond is observed. Computational analysis shows a high energy barrier for silylene insertion, therefore a protonation-deprotonation mechanism is more likely.
UR - http://www.scopus.com/inward/record.url?scp=84884521465&partnerID=8YFLogxK
U2 - 10.1039/c3cc45652h
DO - 10.1039/c3cc45652h
M3 - 文章
AN - SCOPUS:84884521465
SN - 1359-7345
VL - 49
SP - 9440
EP - 9442
JO - Chemical Communications
JF - Chemical Communications
IS - 82
ER -