1266329-41-2Relevant academic research and scientific papers
Grignard reagent/CuI/LiCl-mediated stereoselective cascade addition/cyclization of diynes: A novel pathway for the construction of 1-methyleneindene derivatives
Li, De-Yao,Wei, Yin,Shi, Min
supporting information, p. 15682 - 15688 (2013/11/19)
Diynes containing a cyclopropane group smoothly undergo a novel intramolecular and stereoselective cascade addition/cyclization reaction to produce the corresponding 1-methyleneindene derivatives in moderate to good yields. This interesting transformation is mediated by Grignard reagent/CuI with LiCl as an additive under mild conditions. The obtained product can easily be further functionalized through cyclopropyl ring opening. A plausible reaction mechanism has also been presented on the basis of deuterium labeling and control experiments. Diyne cyclization: Diynes containing a cyclopropane group undergo a novel intramolecular and stereoselective cascade addition/cyclization reaction to produce the corresponding 1-methyleneindene derivatives (see scheme). The transformation proceeds under mild conditions and is promoted by a combination of Grignard reagent Copyright
Simple gold-catalyzed synthesis of benzofulvenes-gem-Diaurated species as "instant dual-activation" precatalysts
Hashmi, A. Stephen K.,Braun, Ingo,Noesel, Pascal,Schaedlich, Johannes,Wieteck, Marcel,Rudolph, Matthias,Rominger, Frank
supporting information; experimental part, p. 4456 - 4460 (2012/06/04)
Alkyl-substituted diynes deliver benzofulvenes in a unique gold-catalyzed reaction. The catalytic cycle involves the formation of gold acetylides by alkynyl C-H activation, the formation of vinylidene gold(I) intermediates by dual activation, and alkyl C-H activation by the vinylidene gold(I) species. gem-Diaurated species obtained from the catalysis reactions prove to be highly active catalysts for these conversions. Copyright
Experimental and computational evidence for gold vinylidenes: Generation from terminal alkynes via a bifurcation pathway and facile C-H insertions
Ye, Longwu,Wang, Yanzhao,Aue, Donald H.,Zhang, Liming
, p. 31 - 34 (2012/02/15)
Facile cycloisomerization of (2-ethynylphenyl)alkynes is proposed to be promoted synergistically by two molecules of BrettPhosAuNTf2, affording tricyclic indenes in mostly good yields. A gold vinylidene is most likely generated as one of the reaction intermediates on the basis of both mechanistic studies and theoretical calculations. Different from the well-known Rh, Ru, and W counterparts, this novel gold species is highly reactive and undergoes facile intramolecular C(sp3)-H insertions as well as O-H and N-H insertions. The formation step for the gold vinylidene is predicted theoretically to be complex with a bifurcated reaction pathway. A pyridine N-oxide acts as a weak base to facilitate the formation of an alkynylgold intermediate, and the bulky BrettPhos ligand in the gold catalyst likely plays a role in sterically steering the reaction toward formation of the gold vinylidene.
Direct synthesis of fused indoles by gold-catalyzed cascade cyclization of diynes
Hirano, Kimio,Inaba, Yusuke,Takahashi, Naoya,Shimano, Masanao,Oishi, Shinya,Fujii, Nobutaka,Ohno, Hiroaki
, p. 1212 - 1227 (2011/04/25)
A direct, concise, and atom-economical synthetic method for the generation of fused indoles, using a gold-catalyzed cascade cyclization of diynes, has been developed. The reaction gave various fused indoles, such as aryl-annulated[a]carbazoles, dihydrobenzo[g]indoles, and azepino-or oxepinoindole derivatives in good to excellent yields, through an intramolecular cascade 5-endo-dig hydroamination followed by a 6-or 7-endo-dig cycloisomerization, without producing theoretical byproduct. Three of the resulting indoles exhibited potent antifungal activities against T. mentagrophytes and T. rubrum, demonstrating the practical application of the described cascade reaction for drug discovery.(Figure Presented)
