Woonphil Baik

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.

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 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.

LiAlH4 Promoted reductive deoxygenation of hydroxybenzyl alcohols via benzoquinone methide intermediates

Abstract Primary and secondary hydroxybenzyl alcohols react with LiAlH 4 in chlorobenzene to give the corresponding alkylphenols. The reaction proceeds through the formation of benzoquinone methide as an intermediate. An example of [4+2] cycloaddition of benzoquinone methide is also reported.

DMSO-AC2O PROMOTED NITRATION OF ISOQUINOLINES. ONE-STEP SYNTHESIS OF 1-NITROISOQUINOLINES UNDER MILD CONDITIONS

1-Nitroisoquinolines were directly prepared from the corresponding isoquinolines with potassium nitrite and acetic anhydride in DMSO in good yields.

SmI2 MEDIATED ALLYLATION OF ALDIMINES WITH ALLYL BROMIDE

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

Photostimulated tert-butylations of difluorinated aromatics involving electron and proton transfers

Abstract Electron transfer chain processes leading to regioselective homolytic tert -butylations for highly electron-deficient benzene derivatives, such as difluorinated acylbenzenes and benzonitriles was established with tert -butylmercury chloride in the presence of 1,4-diazabicyclo[2.2.2]octane.

Chemoselective Reactions of Anthrone with α,β-Unsaturated Ketones

In the presence of ZnCl2, 1,4-conjugated addition of anthrone with α,β-unsaturated ketones proceeded to give mono-Michael adducts, whereas in basic solution it gave bis-Michael adducts.

NEW APPROACH TO P-HYDROXYBENZYLATION OF ARENES VIA A QUINOMETHANE GENERATED IN SITU FROM A MANNICH BASE

p-Hydroxybenzylation of arenes can be performed efficiently using a Mannich base and (MeO)2SO2 at reflux in the presence of ZnCl2.