5418-21-3Relevant articles and documents
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
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.
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
