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Volumn 49, Issue 48, 2010, Pages 9182-9186

Catalytic intermolecular tail-to-tail hydroalkenylation of styrenes with α olefins: Regioselective migratory insertion controlled by a nickel/n-heterocyclic carbene

Author keywords

homogeneous catalysis; insertion; N heterocyclic carbenes; nickel; olefination

Indexed keywords

CARBENES; HOMOGENEOUS CATALYSIS; IMIDAZOL-2-YLIDENE; INSERTION; MIGRATORY INSERTION; MONOSUBSTITUTED ALKENES; N-HETEROCYCLIC CARBENES; OLEFINATION; REGIO-SELECTIVE;

EID: 78649587962     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201001849     Document Type: Article
Times cited : (69)

References (77)
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    • For representative reversals in the regiochemical outcome resulting from using NHCs systems instead of Ni phosphines, see
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    • 13C NMR spectra) contain a significant discrepancy when compared to those of an authentic sample prepared using the Wittig reagent
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    • We did not observe the hetero-hydroalkenylation product from the reaction between cod and styrene. When we tested norbornene, a linear exo-trans-vinylbenzene was obtained in 27% yield, and a second styrene insertion gave the t-t product in 16%, thus suggesting our system cannot override the strong steric bias it offers, and β -hydride elimination steps are more difficult. See the Supporting Information for details
    • We did not observe the hetero-hydroalkenylation product from the reaction between cod and styrene. When we tested norbornene, a linear exo-trans-vinylbenzene was obtained in 27% yield, and a second styrene insertion gave the t-t product in 16%, thus suggesting our system cannot override the strong steric bias it offers, and β -hydride elimination steps are more difficult. See the Supporting Information for details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.