Young Moo Jun

Indium-mediated one-pot reductive conversion of nitroarenes to N-arylacetamides

N-Arylacetamides were prepared in excellent yields from nitroarenes in the presence of acetic anhydride, acetic acid and indium by a one-pot procedure.

Silver(I) ion selective ionophores containing dithiocarbamoyl moieties on steroid backbone

Tweezer-type and non-tweezer-type ionophores containing dithiocarbamoyl groups on a 7-deoxycholic amide or cholane derivatives were designed and synthesized. Potentiometric evaluation of the poly(vinyl chloride) (PVC) membranes containing those deoxycholic amides/cholanes linked with tweezer-type dithiocarbamoyl moieties showed excellent affinity and selectivity to silver(I) ion over alkali, alkaline earth and other transition metal cations. On the other hand, deoxycholic amides/cholanes substituted with one dithiocarbamoyl group, i.e., non-tweezer-type ionophores, resulted in relatively poor potentiometric sensitivity and detection limits. The enhanced potentiometric properties of newly synthesized tweezer-type dithiocarbamoyl containing ionophores have been further improved by employing silver ion complexing reagent in the internal reference solution, which resulted in greatly reduced detection limit ( approximately 100ppt) for the electrodes based on them.

Indium mediated reductive heterocyclization of 2-nitroacylbenzenes or 2-nitroiminobenzenes toward 2,1-benzisoxazoles in aqueous media

2-Nitro-substituted acylbenzenes or iminobenzenes such as 2-nitrobenzaldehydes, 2′-nitroacetophenone, and N-(2-nitrobenzylidene)anilines were cyclized toward 2,1-benzisoxazoles in the presence of 2-bromo-2-nitropropane and indium in an MeOH/H2O solution in excellent yields.

Reductive heterocyclizations via indium–iodine-promoted conversion of 2-nitroaryl imines or 2-nitroarenes to 2,3-diaryl-substituted indazoles

While N-(2-nitrobenzylidene)anilines produced mixtures of 2,1-benzisoxazoles and 3-anilino-2-aryl-2H-indazoles in the presence of indium and iodine in MeOH, N-(2-nitrobenzylidene)anilines were transformed into 3-anilino-2-aryl-2H-indazoles as the predominant major product through the change of the solvent from protic MeOH to aprotic THF. In an indium-mediated one-pot reductive reaction, 2-benzaldehydes and anilines in THF were also successfully transformed into the corresponding indazoles.

Asymmetric Allylation of Aldimines with Indium and (+)‐Cinchonine

Abstract By applying indium and allyl bromide, aldimines were converted into homoallyl amines with excellent yields. The addition of (+)‐cinchonine to the reaction mixture yielded enantioselective allylation with 22–44% ee.

Reductive cyclization of o-nitrophenylazobenzenes to 2-aryl-2H-benzotriazoles by SmI2

Abstract In a mild reaction with SmI2, ortho-nitro substituted phenylazobenzenes have been converted into 2-aryl-2H-benzotriazoles.

INDIUM MEDIATED REDUCTIVE ACYLATIONS OF NITROARENES TOWARDS N,O-DIACYLATED N-ARYLHYDROXYLAMINES*

By applying indium, Ac2O, MeOH, and catalytic amount of InCl3 in CHCl3 solution, nitroarenes were transformed into N,O-diacylated N-arylhydroxylamines in moderate to excellent yields. *Dedicated to Professor Jack W. Timberlake on the occasion of his 60th Birthday.

Synthesis and characterization of 7-deoxycholic amide backbone-based silver(I) ionophores

Four ionophores containing bipyridyl groups on a 7-deoxycholic amide derivative scaffold were designed and synthesized. Potentiometric evaluation of the Poly(vinyl chloride) (PVC) membranes containing those deoxycholic amides bearing bipyridyl moieties with a short linkage showed good affinity to silver(I) ion over alkali, alkaline earth and other transition metal cations. However, two bipyridyl groups flexibly linked to the deoxycholic frame through a long linkage do not result in appreciable potentiometric responses.

SmI2 MEDIATED ALLYLATION OF ALDIMINES WITH ALLYL BROMIDE

In a mild reaction with SmI2, aldimines have been converted into homoallyl amines in good yields.

One-pot aryl-1,4-thiomorpholine 1,1-dioxide synthesis via double 1,4-addition of in situ reduced nitroarenes to divinyl sulfones

One-pot reduction-triggered double aza-Michael type 1,4-addition reactions of various nitroarenes to divinyl sulfones were investigated. In the presence of indium/AcOH in MeOH or in sat. aq NH 4 Cl/MeOH, nitroarenes and divinyl sulfones were cyclized to give 1,4-thiomorpholine 1,1-dioxides.