A simple and regioselective α-bromination of alkyl aromatic compounds by two-phase electrolysis

Raju, T.; Kulangiappar, K.; Kulandainathan, M. Anbu; Muthukumaran, A.

doi:10.1016/j.tetlet.2005.08.044

Cited by 32 publications

(11 citation statements)

References 12 publications

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“…Mono - 415 and di - 416 benzylic bromination of toluene derivatives can be achieved depending on the reaction conditions. The formation of HOBr was invoked in each case; bromination at the nucleus of more electron-rich arenes is the major competing reaction.…”

Section: Anodic Oxidationmentioning

confidence: 99%

Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance

2017

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Section: Anodic Oxidationmentioning

confidence: 99%

Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance

2017

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“…An early report from Raju and collaborators demonstrated the applicability of electrochemical conditions for the direct C( sp 3 )−H bromination of alkylarenes (Scheme 46). [94] The reaction was carried out in an undivided cell via two‐phase electrolysis, using chloroform and aqueous sodium bromide solution (60%) containing a catalytic amount of HBr. Benzyl bromides were obtained in good to excellent yields.…”

Section: Electrochemical Benzylic C(sp3)−h Functionalizationmentioning

confidence: 99%

Photochemical and Electrochemical Strategies towards Benzylic C−H Functionalization: A Recent Update

et al. 2021

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Transition metal-catalysed processes have been widely used for the functionalization of inert CÀ H bonds. Strategies for the functionalization of the benzylic CÀ H position having a relatively weak CÀ H bond (bond dissociation energy~80-90 kcal/mol) differ from the inert aliphatic and aromatic CÀ H positions with stronger CÀ H bonds. The recent advances in the direct activation of the benzylic position through the generation of C(sp 3) radicals have demonstrated the potential of electrochemistry and photochemistry as a means for constructing new chemical bonds. This review will cover the recent progress of benzylic CÀ H functionalization through organic radical strategies employing photochemistry and electrochemistry as sustainable tools. In addition, the mechanistic details of the typical reactions have been included which, in turn, will help the researchers to look at this promising area from a different perspective towards new discoveries and often hidden opportunities. 2.1. C(sp 3)À C Bond Formation 2.2. C(sp 2)À O and C(sp 3)À O Bond Formation 2.3. C(sp 3)À N Bond Formation 2.4. C(sp 3)À S Bond Formation 2.5. C(sp 3)À Halogen Bond Formation 3. Electrochemical Benzylic C(sp 3)À H Functionalization 3.1. C(sp 3)À C Bond Formation 3.2. C(sp 3)À O Bond Formation 3.3. C(sp 3)À N Bond Formation 3.4. C(sp 3)À P Bond Formation 3.5. C(sp 3)À Halogen Bond Formation 4. Benzylic C(sp 3)À H Functionalization via Synthetic Photoelectrochemistry 5. Conclusions and Outlook

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“…[15,16] Hence we studied the orientation of bromine in 4-metoxy toluene, which has both the methyl (prefers side-chain bromination) and methoxy (prefers nuclear bromination) groups. After passing a charge of 6 F=mol, 3-bromo-4-methoxy-benzyl bromide is obtained in 86% yield as shown in Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

Nuclear Versus Side-Chain Bromination of 4-Methoxy Toluene by an Electrochemical Method

Kulangiappar

Anbukulandainathan

Raju

2014

Synthetic Communications

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The electrochemical bromination of 4-methoxy toluene by two-phase electrolysis yields 3-bromo 4-methoxy toluene at first, which subsequently undergoes side-chain bromination to give 3-bromo 4-methoxy benzyl bromide as a final product in 86% yield. The two-phase electrolysis consists of 25-50% NaBr as aqueous electrolyte and CHCl 3 containing aromatic compound as organic phase. The reaction temperature is maintained at 10-25 C. The probable orientation of bromine atom in an alkyl aromatic compound (nuclear versus side chain) is explained from the experimental result.

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A simple and regioselective α-bromination of alkyl aromatic compounds by two-phase electrolysis

Cited by 32 publications

References 12 publications

Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance

Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance

Photochemical and Electrochemical Strategies towards Benzylic C−H Functionalization: A Recent Update

Nuclear Versus Side-Chain Bromination of 4-Methoxy Toluene by an Electrochemical Method

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