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Tetrahedron | 1999

SIMPLE AND PRACTICAL HALOGENATION OF ARENES, ALKENES AND ALKYNES WITH HYDROHALIC ACID/H2O2 (OR TBHP)

Nivrutti B. Barhate; Anil S. Gajare; Radhika D. Wakharkar; Ashutosh V. Bedekar

Abstract A simple protocol for the halogenation of arenes utilizing a combination of aqueous hydrogen peroxide (34 %) or tert-butylhydroperoxide (70 %) and hydrohalic acid is presented. A similar procedure of oxyhalogenation involving the in situ generation of positive halogen reagents is applied for the preparation of vicinal trans-dibromoalkanes and dichloroalkanes from alkenes. The reaction of alkenes with a combination of hydrochloric acid and hydrobromic acid with hydrogen peroxide gave a mixture of 1-bromo 2-chloro alkanes and 1,2-dibromoalkanes. Oxidative bromination of alkynes is also reported under similar conditions.


Tetrahedron Letters | 1998

SIMPLE AND EFFICIENT CHLORINATION AND BROMINATION OF AROMATIC COMPOUNDS WITH AQUEOUS TBHP (OR H2O2) AND A HYDROHALIC ACID

Nivrutti B. Barhate; Anil S. Gajare; Radhika D. Wakharkar; Ashutosh V. Bedekar

A combination of aqueous tert-butylhydroperoxide (70%) or hydrogen peroxide (34%) and a hydrohalic acid was found effective in chlorination and bromination of aromatic compounds.


Tetrahedron Letters | 1997

Facile regeneration of carbonyl compounds from oximes and tosylhydrazones with TBHP

Nivrutti B. Barhate; Anil S. Gajare; Radhika D. Wakharkar; A. Sudalai

Abstract 70% tert-Butyl hydroperoxide (TBHP) has been found to be an efficient and selective reagent for the mild oxidative cleavage of the CN of oximes and tosylhydrazones to yield their corresponding carbonyl compounds


Chemical Communications | 2004

Application of a diphosphinidenecyclobutene ligand in the solvent-free copper-catalysed amination reactions of aryl halidesElectronic supplementary information (ESI) available: details of general procedure for the solvent amination reaction; characterisation data of the products listed in Table 1 and Table 2. See http://www.rsc.org/suppdata/cc/b4/b408232j/

Anil S. Gajare; Kozo Toyota; Masaaki Yoshifuji; Fumiyuki Ozawa

1,2-Diphenyl-3,4-bis[(2,4,6-tri-tert-butylphenyl)phosphinidene]cyclobutene was used as an additive ligand in copper-catalysed amination reactions of halobenzenes with amines in the presence of base to afford the corresponding secondary or tertiary amines in good to excellent yields.


Tetrahedron Letters | 2000

A mild procedure for the clay catalyzed selective removal of the tert-butoxycarbonyl protecting group from aromatic amines

Nadim S. Shaikh; Anil S. Gajare; Vishnu H. Deshpande; Ashutosh V. Bedekar

Abstract The application of solid acidic catalysts for the selective removal of N-Boc protection is presented in this report. Montmorillonite K10 was found to be an effective catalyst in removing aromatic N-Boc groups while leaving aliphatic N-Boc amines untouched.


Green Chemistry | 2002

EPZ-10 catalyzed regioselective transformation of alkenes into β-iodo ethers, iodohydrins and 2-iodomethyl-2,3-dihydrobenzofurans

Vishal A. Mahajan; Popat D. Shinde; Anil S. Gajare; M. Karthikeyan; Radhika D. Wakharkar

An efficient method for the regioselective synthesis of β-iodo ethers and iodohydrines from styrene, indene and dihydronaphthalene in presence of EPZ-10R has been presented wherein only 0.5 equivalent iodine (I2) has been used. Similarly, o-allylphenols are converted to 2-iodomethyl-2,3-dihydrobenzofurans in high yields. This demonstrates a clean green chemical transformation with significant atom economy.


Synthetic Communications | 2002

MICROWAVE ACCELERATED TETRAHYDROPYRANYLATION AND DETETRAHYDROPYRANYLATION OF ALCOHOLS, PHENOLS, AND THIOLS CATALYZED BY HYDRATED ZIRCONIA

Anil S. Gajare; Dhananjay P. Sabde; Murlidhar S. Shingare; Radhika D. Wakharkar

ABSTRACT A solvent free and expeditious method for tetrahydropyranylation and detetrahydropyranylation of alcohols, phenols and thiols is described using hydrated zirconia and 3,4-dihydro-2H-pyran (DHP). A comparison of this microwave-accelerated reaction with conventional heating condition is also presented.


Journal of The Chemical Society-perkin Transactions 1 | 2000

Clay catalyzed conversion of isatoic anhydride to 2-(o-aminophenyl)oxazolines

Anil S. Gajare; Nadim S. Shaikh; Gowda K. Jnaneshwara; Vishnu H. Deshpande; Thottappilli Ravindranathan; Ashutosh V. Bedekar

A simple and environmentally safe procedure for the preparation of 2-(o-aminophenyl)oxazolines from isatoic anhydride is presented. A series of chiral derivatives of the title compound is prepared in moderate yield via natural kaolinitic clay catalyzed reactions with optically pure 2-aminoalcohols. Reaction of polymer-supported isatoic anhydride under these conditions with chiral 2-aminoalcohols proceeds to furnish polymer-anchored analogues.


Journal of The Chemical Society-perkin Transactions 1 | 2000

Microwave accelerated selective and facile deprotection of allyl esters catalyzed by Montmorillonite K-10

Anil S. Gajare; Nadim S. Shaikh; Bhushan K. Bonde; Vishnu H. Deshpande

Carboxylic acids are regenerated from their corresponding substituted allyl esters by Montmorillonite K-10 using microwave irradiation under solvent free conditions to afford enhanced yields and reduced reaction times compared to thermal conditions.


Journal of The Chemical Society-perkin Transactions 1 | 1998

TRANSDITHIOACETALIZATION OF ACETALS, KETALS, OXIMES, ENAMINES AND TOSYLHYDRAZONES CATALYSED BY NATURAL KAOLINITIC CLAY

G. K. Jnaneshwara; N. B. Barhate; A. Sudalai; Vishnu H. Deshpande; R. D. Wakharkar; Anil S. Gajare; M. S. Shingare; R. Sukumar

Natural kaolinitic clay efficiently catalyses the transdithioacetalization of acetals, ketals, oximes, enamines and tosylhydrazones with ethane-1,2-dithiol and propane-1,3-dithiol to produce the corresponding dithiolanes in high yields.

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