5418-21-3Relevant academic research and scientific papers
Regioselective synthesis of indenols via nickel-catalyzed carbocyclization reaction
Rayabarapu, Dinesh Kumar,Yang, Chun-Hui,Cheng, Chien-Hong
, p. 6726 - 6731 (2003)
2-Halophenyl ketones 1a-e (1a, o-IC6H4COCH 3) undergo carbocyclization with alkyl propiolates (2a, CH 3(CH2)4C≡CCO2CH3; 2b, TMSC≡CCO2Et 2c, CH3C≡CCO 2CH3; 2d, CH3OCH2C≡CCO 2CH3; 2e, CH3(CH2) 3C≡CCO2CH3; 2f, PhC≡CCO 2CH3; and 2g, (CH3)3C≡CCO 2CH3) in the presence of Ni(dppe)Br2 and zinc powder in acetonitrile at 80 °C to afford the corresponding indenol derivatives 3a-m with remarkable regioselectivity in good to excellent yields. The nickel-catalyzed carbocyclization reaction was successfully extended to other simple disubstituted alkynes. Thus, the reaction of2-halophenyl ketones 1a - e with disubstituted alkynes (2h, PhC≡CPh; 2i, CH3C 6H4C≡CC6H4-CH3; 2j, CH3CH2C≡CCH2CH3; 2k, PhC≡CCH3; 21, TMSC≡CCH3; and 2m, PhC≡C(CH2)3CH3) proceeded smoothly to afford the corresponding indenols 4a-t in good to excellent yields. For unsymmetrical alkynes 2k-m, the carbocyclization gave two regioisomers with regioselectivities ranging from 1:2 to 1:12 depending on the substituents on the alkyne and on the aromatic ring of halophenyl ketone. A possible mechanism for this nickel-catalyzed carbocyclization reaction is also proposed.
Reactions of ortho-manganated aryl-ketones, aldehydes and amides with alkynes; a new synthesis of inden-1-ols and indenones
Robinson, Nicholas P.,Main, Lyndsay,Nicholson, Brian K.
, p. C37 - C39 (1989)
ν2-(2-Acetylphenyl)tetracarbonylmanganese reacts directly in benzene with diphenylacetylene to give 2,3-diphenyl-1-methylinden-1-ol in 97percent yield, while ortho-manganeted N,N-dimethylbenzamide or p-dimethylaminobenzaldehyde react similarly
Cobalt-catalyzed regioselective [3+2] annulation of ortho-formyl and acetyl substituted phenylboronic acids with alkynes
Ueda, Mitsuhiro,Ueno, Tamami,Suyama, Yuki,Ryu, Ilhyong
supporting information, p. 2972 - 2974 (2017/07/11)
Treatment of alkynes with ortho-formyl and acetyl phenylboronic acids in the presence of a cobalt catalyst resulted in the formation of 2,3-disubstituted indenols in good yields. When aryl silyl alkynes were used, 2-aryl-3-silyl indenols were obtained reg
Palladium-catalyzed annulation of internal alkynes in aqueous medium
Ang, Wei Jie,Tai, Chih-Hsuan,Lo, Lee-Chiang,Lam, Yulin
, p. 4921 - 4929 (2014/01/23)
To facilitate precatalyst recovery and reuse, we have developed a fluorous, oxime-based palladacycle 1 and demonstrated that it is a very efficient and versatile precatalyst for carbo- and heteroannulation of internal alkynes with functionalized aryl halides in aqueous medium. A uniform reaction condition for these annulation reactions was also developed.
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
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.
Synthesis of 1H-inden-1-ol derivatives via rhodium-catalyzed annulation of o-acylphenylboronic acids with alkynes
Matsuda, Takanori,Makino, Masaomi,Murakami, Masahiro
, p. 1416 - 1417 (2007/10/03)
A rhodium-catalyzed annulation reaction of o-formyl-phenylboronic acid with alkynes occurred regioselectively at room temperature to give substituted 1H-inden-1-ol derivatives. o-Acetylphenylboronic acid also underwent the annulation reaction at 80°C to a
Cobalt-catalyzed regioselective carbocyclization reaction of o-iodophenyl ketones and aldehydes with alkynes, acrylates, and acrylonitrile: A facile route to indenols and indenes
Chang, Kuo-Jui,Rayabarapu, Dinesh Kumar,Cheng, Chien-Hong
, p. 4781 - 4787 (2007/10/03)
An efficient cobalt-catalyzed carbocylization for the synthesis of indenols and indenes and a new method for reductive decyanation are described. 2-Iodophenyl ketones and aldehydes 1a-g undergo carbocyclization with various disubstituted alkynes 2a-k in the presence of Co(dppe)I2 and zinc powder in acetonitrile at 80 °C for 3 h to afford the corresponding indenol derivatives 3a-s and 4a-m in good to excellent yields. For some unsymmetrical alkynes, the carbocyclization was remarkably regioselective, affording a single regioisomer. The cobalt-catalyzed carbocyclization reaction was successfully extended to the synthesis of indene derivatives. Thus, the reaction of 2-iodophenyl ketones and aldehydes (1) with acrylates H2C=CHCO 2R (7a-d) and acrylonitrile H2C= CHCN (7e) proceeds smoothly in the presence of Co(dppe)Cl2/dppe and zinc powder in acetonitrile at 80 °C for 24 h to afford the corresponding indenes 8a-k and 9a-c in moderate to good yields. Interestingly, when 7e was employed for the carbocylization, reductive decyanation also occurred to give an indene derivative without the cyano functionality. A possible mechanism for this cobalt-catalyzed carbocyclization reaction is also proposed.
Cobalt-Catalyzed Carbocyclization of o-Iodobenzaldehydes and o-Iodophenylketones with Alkynes
Chang, Kuo-Jui,Rayabarapu, Dinesh Kumar,Cheng, Chien-Hong
, p. 3963 - 3966 (2007/10/03)
(Equation Presented) Treatment of various o-iodobenzaldehydes and o-iodophenyl ketones with alkynes in the presence of Co(dppe)l2 and Zn powder in acetonitrile at 80°C afforded the corresponding indenols in moderate to excellent yields with exceedingly high regioselectivity. For most unsymmetrical alkynes tested, the carbocyclization gave a single regioisomer.
