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Volumn 19, Issue 13, 2013, Pages 4287-4299

A new class of remote N-heterocyclic carbenes with exceptionally strong σ-donor properties: Introducing benzo[c]quinolin-6-ylidene

Author keywords

N heterocyclic carbenes; structure elucidation; transition metals

Indexed keywords

CARBENE COMPLEXES; COUPLING PRODUCT; ELECTRON-DONATING; FACILE SYNTHESIS; N-HETEROCYCLIC CARBENES; OXIDATIVE ADDITIONS; STRUCTURE ELUCIDATION; TRIFLUOROMETHANESULFONATE;

EID: 84875125749     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201203294     Document Type: Article
Times cited : (22)

References (117)
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    • NHCs are generally perceived as good σ donors and relatively poor π acceptors. Even though the importance of the π-acceptor properties in NHCs is not yet fully understood and appreciated, reports have been made that the course of a mechanistically distinct gold-catalysed process can be determined solely by modulating the p-acceptor properties of the ancillary NHC ligand. See
    • NHCs are generally perceived as good σ donors and relatively poor π acceptors. Even though the importance of the π-acceptor properties in NHCs is not yet fully understood and appreciated, reports have been made that the course of a mechanistically distinct gold-catalysed process can be determined solely by modulating the p-acceptor properties of the ancillary NHC ligand. See:, M. Alcarazo, T. Stork, A. Anoop, W. Thiel, A. Fürstner, Angew. Chem. 2010, 122, 2596
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    • Kinetic stabilisation of the carbene centre by sterically demanding N,N'-substitution pattern is much more important for saturated imidazolidin-2-ylidenes than for their unsaturated imidazolin-2-ylidenes counterparts. For example, the reductive desulfurisation of an imidazolidin-2-thione with sterically demanding substituents such as R=tBu resulted in the formation of the corresponding stable carbene. In contrast, when sterically less demanding substituents such as R=Me, where present, only the dimerisation product entetraamine was obtained. See
    • Kinetic stabilisation of the carbene centre by sterically demanding N,N'-substitution pattern is much more important for saturated imidazolidin-2-ylidenes than for their unsaturated imidazolin-2-ylidenes counterparts. For example, the reductive desulfurisation of an imidazolidin-2-thione with sterically demanding substituents such as R=tBu resulted in the formation of the corresponding stable carbene. In contrast, when sterically less demanding substituents such as R=Me, where present, only the dimerisation product entetraamine was obtained. See:, M. K. Denk, A. Thadani, K. Hatano, A. J. Lough, Angew. Chem. 1997, 109, 2719
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.