849799-68-4Relevant articles and documents
Dual Gold-Catalyzed Three-Component Reaction: Efficient Synthesis of Indene-Fused Esters, Acids, and Lactones through Gold Vinylidene Intermediates
Yu, Congjun,Ma, Xiaodong,Chen, Bin,Tang, Bencan,Paton, Robert S.,Zhang, Guozhu
, p. 1561 - 1565 (2017/04/01)
A dual gold(I)-catalyzed three-component reaction was developed to prepare indene-fused carboxylic acid derivatives from diynes, alcohols, and pyridine N-oxides in both inter- and intramolecular fashions. The pyridine N-oxides were found to exhibit distinct selectivity unlike the α-oxo gold carbene intermediates in the well-developed gold-catalyzed oxidative functionalization of alkynes. Experimental studies and DFT calculations support double nucleophilic substitution of a gold vinylidene intermediate.
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
Ruthenium-catalyzed aromatization of enediynes via highly regioselective nucleophilic additions on a π-alkyne functionality. A useful method for the synthesis of functionalized benzene derivatives
Odedra, Arjan,Wu, Chang-Jung,Pratap, Taduri Bhanu,Huang, Chun-Wei,Ran, Ying-Fen,Liu, Rai-Shung
, p. 3406 - 3412 (2007/10/03)
TpRu(PPh3)(CH3CN)2PF6 (10 mol %) catalyst effected the nucleophilic addition of water, alcohols, aniline, acetylacetone, pyrroles, and dimethyl malonate to unfunctionalized enediynes under suitable conditions (100 °C, 12-24 h) and gave functionalized benzene products in good yields. In this novel cyclization, nucleophiles very regioselectively attack the internal C1′ alkyne carbon of enediynes to give benzene derivatives as a single regioisomer. Experiments with methoxy substituents exclude the possible involvement of naphthyl cations as reaction intermediates in the cyclization of (o-ethynylphenyl) alkynes. Deuterium-labeling experiments indicate that the catalytically active species is ruthenium-π-alkyne rather than ruthenium-vinylidene species. This hypothesis is further confirmed by the aromatization of o-(2′-iodoethynyl)phenyl alkynes with alcohols. We propose a nucleophilic addition/insertion mechanism for this nucleophilic aromatization on the basis of a series of experiments.
