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Isolation of an N-Heterocyclic Carbene Complex of a Borasilene

Isolation of an N-Heterocyclic Carbene Complex of a Borasilene

Daniel Franz, Tibor Szilvási, Alexander Pöthig, Shigeyoshi Inoue

Chemistry. 2019 Aug 22;25(47):11036-11041.

PMID: 31241215

Abstract:

Borasilenes, that is complexes which contain a boron-silicon double bond, have scarcely been isolated to date. In pursuit of such species, (Me3 Si)3 SiB(Cl)NHI (2, NHI=bulky N-heterocyclic imine) was prepared and treated with KOtBu to achieve formal extrusion of ClSiMe3 . The formation of an elusive borasilene (3int ) is postulated and it was verified by isolation of the N-heterocyclic carbene adduct (Me3 Si)2 SiB(I Me 4 )NHI (4, I Me 4 =1,3,4,5-tetramethyl-imidazolin-2-ylidene). X-ray crystallographic study and theoretical calculations on 4 diagnosed a boron-silicon double bond with marked zwitterionic character. The negative charge resides at the Si atom which marks the apex of a trigonal pyramid. Structural comparison of 4 with boron cation congeners (5+ , 6+ ) suggests that the positive charge is mainly located at the trigonal planar-coordinated B center. The conversion of 4 with pinacolborane (HBpin, 2 equiv) resulted in cleavage of the double bond to produce (Me3 Si)2 Si(Bpin)2 and (NHI)BH2 (I Me 4 ).

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP1269802972	NHI-2		1269802-97-2	Price

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