The utility of indium in aqueous medium radical reactions.

Indium-mediated radical reactions proceed in the absence of toxic tin hydride, providing a new carbon-carbon bond-forming method in aqueous media. Herein, the results of experiments to probe the utility of indium as a radical initiator in reactions in aqueous media are reported. The indium-mediated tandem reactions also proceed smoothly via two carbon-carbon bond-forming processes for the preparation of various types of functionalized cyclic compounds.

[1]  V. Nair,et al.  Indium- and gallium-mediated carbon-carbon bond-forming reactions in organic synthesis , 2004 .

[2]  H. Miyabe,et al.  Zinc-mediated radical reaction of glyoxylic oxime ether and hydrazone in aqueous media: asymmetric synthesis of α-amino acids , 2003 .

[3]  H. Togo,et al.  Zinc- and Indium-Mediated Ring-Expansion Reaction of α-Halomethyl Cyclic β-Keto Esters in Aqueous Alcohol , 2003 .

[4]  Y. Takemoto,et al.  Regioselectivity in palladium-indium iodide-mediated allylation reaction of glyoxylic oxime ether and N-sulfonylimine. , 2003, The Journal of organic chemistry.

[5]  H. Miyabe,et al.  Tandem carbon-carbon bond-forming radical addition-cyclization reaction of oxime ether and hydrazone. , 2003, The Journal of organic chemistry.

[6]  H. Miyabe,et al.  Carbon–carbon bond construction on solid support: triethylborane-induced radical reactions of oxime ethers , 2003 .

[7]  V. Nair,et al.  Indium/indium trichloride mediated pinacol cross-coupling reaction of aldehydes and chalcones in aqueous media: a facile stereoselective synthesis of substituted but-3-ene-1,2-diols , 2002 .

[8]  N. Fujii,et al.  Indium-mediated atom-transfer cyclizations and reductive cyclizations , 2002 .

[9]  G. Friestad Addition of carbon-centered radicals to imines and related compounds , 2001 .

[10]  Y. Ling,et al.  Indium-mediated tandem dimerization and cyclization of nitrqones and aldimines to 3-arylaminodihydrobenzofurans under aqueous conditions , 2001 .

[11]  J. Ko,et al.  Indium-mediated reductive coupling of acyl cyanides: a convenient synthesis of 1,2-diketones , 2000 .

[12]  Ueda,et al.  Free-radical reaction of imine derivatives in water , 2000, The Journal of organic chemistry.

[13]  Chao-Jun Li,et al.  Organic syntheses using indium-mediated and catalyzed reactions in aqueous media , 1999 .

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

[15]  Tomoaki Nakamura,et al.  Triethylborane-Mediated Atom Transfer Radical Cyclization Reaction in Water , 1998 .

[16]  G. Keum,et al.  Indium mediated pinacol coupling reaction of aromatic aldehydes in aqueous media , 1998 .

[17]  O. Yamazaki,et al.  Novel Water-Soluble Organosilane Compounds as a Radical Reducing Agent in Aqueous Media , 1997 .

[18]  Chao‐Jun Li Aqueous Barbier-Grignard Type Reaction: Scope, Mechanism, and Synthetic Applications , 1996 .

[19]  Chao-Jun Li Organic reactions in aqueous media - with a focus on carbon-carbon bond formation , 1993 .