论文信息 - Dehalogenation and Barbier-type hydroxyalkylation of π-deficient haloheterocycles using indium

Dehalogenation and Barbier-type hydroxyalkylation of π-deficient haloheterocycles using indium

The reaction of π-deficient haloheterocycles with indium metal in water gave corresponding dehalogenated heterocycles. The use of diluted hydrochloric acid instead of water accelerated the reductive reactivity of indium metal. Furthermore, Barbier-type additions proceeded by reactions of α-iodoheterocycles with indium in the presence of pivalaldehyde.

Yukiko Takahashi | Eri Fukuda | O. Sugimoto | K. Tanji | N. Hirasawa

[1] Yukiko Takahashi,et al. Indium-mediated dehalogenation of haloheteroaromatics in water , 2008 .

[2] M. Oyama,et al. Stereoselective synthesis of 3-alkylideneoxindoles using tandem indium-mediated carbometallation and palladium-catalyzed cross-coupling reactions , 2005 .

[3] Min Young Cho,et al. Homocoupling of Aryl Iodides and Bromides Using a Palladium/Indium Bimetallic System , 2005 .

[4] O. Sugimoto,et al. The tellurium–lithium exchange reaction: selective functionalization of electron-deficient heteroaromatics , 2001 .

[5] M. R. Pitts,et al. Indium metal as a reducing agent in organic synthesis , 2001 .

[6] M. Yus,et al. Naphthalene-catalysed Lithiation of Chlorinated Nitrogenated Aromatic Heterocycles and Reaction with Electrophiles , 2000 .

[7] B. Ranu,et al. Indium promoted reductive homocoupling of alkyl and aryl halides , 1998 .

[8] Chao-Jun Li,et al. Organometallic reactions in aqueous media with indium , 1991 .

[9] P. G. Gassman,et al. The ortho functionalization of aromatic amines. Benzylation, formylation, and vinylation of anilines , 1978 .

[10] E. Allred,et al. Quinoxalines. I. Preparation and Stereochemistry of Decahydroquinoxalines , 1960 .

[11] H. Gilman,et al. Organolithium Compounds of Pyridine and Quinoline , 1940 .