1261085-87-3Relevant academic research and scientific papers
Carboranes as Aryl Mimetics in Catalysis: A Highly Active Zwitterionic NHC-Precatalyst
Selg, Christoph,Neumann, Wilma,L?nnecke, Peter,Hey-Hawkins, Evamarie,Zeitler, Kirsten
supporting information, p. 7932 - 7937 (2017/06/19)
Modern catalysis takes advantage of aryl-based interactions to tune and control reactions. In the design of N-heterocyclic-carbene catalysts, both the electronic and steric nature of the nitrogen substituents play a crucial role. Although hydrocarbon-based systems and especially aryl residues have contributed considerably to overcome multifaceted catalytic challenges, the unique properties of carborane moieties, including delocalized charge, potential planar chirality, and well-known thermodynamic stability, offer unprecedented opportunities to develop new catalysts while being employed as aryl mimetics. We report a straightforward synthetic route to a novel zwitterionic triazolium-based N-heterocyclic carbene (NHC) precatalyst bearing a 7,8-dicarba-nido-undecaboranyl substituent. The catalyst's excellent activity and its broad applicability are demonstrated in a wide range of organocatalytic transformations. Comparison of the performance with known N-aryl NHC catalysts offers preliminary insights into the stereoelectronic nature of this nido-carboranyl substituent.
Direct β-activation of saturated aldehydes to formal michael acceptors through oxidative NHC catalysis
Mo, Junming,Shen, Liang,Chi, Yonggui Robin
supporting information, p. 8588 - 8591 (2013/09/12)
Without detours: Oxidative catalysis mediated by N-heterocyclic carbenes (NHCs) enables the direct β-carbon functionalization of saturated aldehydes (see scheme). The reaction proceeds through two sequential oxidative steps to generate α,β-unsaturated tri
N-heterocyclic carbene catalyzed reactions of α-bromo-α,β- unsaturated aldehydes/α,β-dibromoaldehydes with 1,3-dinucleophilic reagents
Yao, Changsheng,Wang, Donglin,Lu, Jun,Li, Tuanjie,Jiao, Weihui,Yu, Chenxia
supporting information; experimental part, p. 1914 - 1917 (2012/03/22)
Carbenes ring true: N-Heterocyclic carbene (NHC) catalyzed reactions of α-bromo-α,β-unsaturated aldehydes/α,β- dibromoaldehydes with 1,3-dinucleophilic reagents, such as 1,3-dicarbonyl compounds, β-enamino ketones, and β-enamino esters through umpolung processes gave functionalized 3,4-dihydropyranones and 3,4-dihydropyridinones (see scheme). The availability of the starting materials, lack of external oxidant, and usefulness of the products make this strategy attractive.
Nhc-catalyzed michael addition to α,β-unsaturated aldehydes by redox activation
De Sarkar, Suman,Studer, Armido
supporting information; experimental part, p. 9266 - 9269 (2011/02/25)
Through oxidative carbene catalysis the reactivity of enals can be reversed at the β position from the typical electrophilic to nucleophilic (homoenolate chemistry) further to electrophilic reactivity by two consecutive umpolung processes. These redox-act
