54365-72-9Relevant academic research and scientific papers
Transfer hydrogenation of isoquinolinium salts catalyzed by a rhodium complex
Wu, Jiashou,Liao, Jian,Zhu, Jin,Deng, Jingen
, p. 2059 - 2062 (2008/02/05)
Regio- and chemoselective transfer hydrogenation of isoquinolinium salts catalyzed by [Cp*RhCl2]2 using HCOOH-Et3N (5:2) as a hydrogen source was realized. A variety of N-methyl- and N-benzyl-1,2,3,4-tetrahydroisoquinoline
Indium metal as a reducing agent in organic synthesis
Pitts,Harrison,Moody
, p. 955 - 977 (2007/10/03)
The low first ionisation potential (5.8 eV) of indium coupled with its stability towards air and water, suggest that this metallic element should be a useful reducing agent for organic substrates. The use of indium metal for the reduction of C=N bonds in imines, the heterocyclic ring in benzo-fused nitrogen heterocycles, of oximes, nitro compounds and conjugated alkenes and the removal of 4-nitrobenzyl protecting groups is described. Thus the heterocyclic ring in quinolines, isoquinolines and quinoxalines is selectively reduced using indium metal in aqueous ethanolic ammonium chloride. Treatment of a range of aromatic nitro compounds under similar conditions results in selective reduction of the nitro groups; ester, nitrile, amide and halide substituents are unaffected. Likewise indium in aqueous ethanolic ammonium chloride is an effective method for the deprotection of 4-nitrobenzyl ethers and esters. Indium is also an effective reducing agent under non-aqueous conditions and α-oximino carbonyl compounds can be selectively reduced to the corresponding N-protected amine with indium powder, acetic acid in THF in the presence of acetic anhydride or di-tert-butyl dicarbonate. Conjugated alkenes are also reduced by indium in THF-acetic acid.
