42454-94-4Relevant academic research and scientific papers
Ruthenium(II)/N-heterocyclic carbene catalyzed [3+2] carbocyclization with aromatic N-H ketimines and internal alkynes
Zhang, Jing,Ugrinov, Angel,Zhao, Pinjing
supporting information, p. 6681 - 6684 (2013/07/26)
Convenient and highly efficient: Indenamines were synthesized using the title reaction, which occurs at ambient temperature, in the absence of oxidants or other metal salts, and in nonpolar solvents. A proposed mechanism involves imine-directed activation
Ruthenium-catalyzed regioselective cyclization of aromatic ketones with alkynes: An efficient route to indenols and benzofulvenes
Chinnagolla, Ravi Kiran,Jeganmohan, Masilamani
supporting information; experimental part, p. 417 - 423 (2012/02/04)
The reactions of substituted acetophenones with diphenylacetylene in the presence of [{RuCl2(p-cymene)}2] (2 mol-%), AgSbF 6 (8 mol-%), and Cu(OAc)2·H2O (25 mol-%) in 1,2-dichloroethane at 120 °C for
Regioselective synthesis of indenols by rhodium-catalyzed C-H activation and carbocyclization of aryl ketones and alkynes
Muralirajan, Krishnamoorthy,Parthasarathy, Kanniyappan,Cheng, Chien-Hong
supporting information; experimental part, p. 4169 - 4172 (2011/06/24)
Ketones and alkynes join together: The catalytic title reaction proceeds rapidly at 120 °C and requires only 1 hour for completion (see scheme). The reaction mechanism likely involves chelation-assisted ortho C-H activation, insertion of the alkyne moiety, carbocyclization, and protonation. Cp=pentamethylcyclopentadienyl. Copyright
Diverse strategies toward indenol and fulvene derivatives: Rh-catalyzed C-H activation of aryl ketones followed by coupling with internal alkynes
Patureau, Frederic W.,Besset, Tatiana,Kuhl, Nadine,Glorius, Frank
supporting information; experimental part, p. 2154 - 2156 (2011/04/23)
The synthesis of indenols and fulvenes was achieved through Rh-catalyzed C-H bond activation of simple and diverse aryl ketone derivatives and subsequent coupling with internal alkynes. The process was found to involve either an α or γ dehydration step, d
Indenols, indenones and (arylcyclohexadienyl)Mn(CO)3 π-complexes from the thermally promoted reactions of alkynes with ortho-Mn(CO)4 aryl ketone, amide, ester and aldehyde derivatives
Robinson, Nicholas P.,Depree, Gary J.,De Wit, Rene W.,Main, Lyndsay,Nicholson, Brian K.
, p. 3827 - 3837 (2007/10/03)
Thermally promoted reactions of a range of alkynes with the orthomanganated acetophenone (η2-2-acetylphenyl)Mn(CO)4 generally give 1H-inden-1-ols in good yield; effects of substituents and solvent on these reactions are reported, along with the crystal structure of 1-methyl-2,3- diphenyl-1H-inden-1-ol. The corresponding orthomanganated benzophenone similarly gives the indenol with diphenylacetylene but by exception, orthomanganated 3-acetylthiophene with phenylacetylene reacts via triple alkyne insertion and cyclisation, shown by crystal structure determination of the π-complex product [(1,2,3,4,5-η)-2-(3-acetylthien-2-yl)-1,3,5- triphenylcyclohexadienyl]tricarbonylmanganese. Corresponding orthomanganated derivatives of N,N-dimethylbenzamide, methyl 3,4,5-trimethoxybenzoate and 4-dimethylaminobenzaldehyde all give indenones with diphenylacetylene, but with (excess) acetylene only the aldehyde gives an indenone, the amide and ester giving instead [(1,2,3,4,5-η)-6-arylcyclohexadienyl]Mn(CO)3 complexes. 1H NMR analysis of these complexes shows H at C6 to be on the same face of the cyclohexadienyl ring as Mn(CO)3 (endo-6-H; exo 6-aryl) as expected from three successive syn additions of alkyne at metallated carbon followed by intramolecular syn addition of alkene in the final cyclisation stage.
