TBCA mediated microwave-assisted Hofmann rearrangement

Miranda, Leandro S. M.; Silva, Thayane Rabello da; Crespo, Lívia T. C.; Esteves, Pierre M.; Matos, Louise F. de; Diederichs, Carla C.; Souza, Rodrigo O. M. A. de

doi:10.1016/j.tetlet.2011.01.126

Cited by 12 publications

(3 citation statements)

References 24 publications

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“…Tribromoisocyanuric acid can be used for the Hofmann rearrangement reaction . Miranda developed a protocol for microwave-assisted Hofmann rearrangement mediated by tribromoisocyanuric acid/KOH/MeOH.…”

Section: Rearrangement Reactionsmentioning

confidence: 99%

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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Bromination is one of the most important transformations in organic synthesis and can be carried out using bromine and many other bromo compounds. Use of molecular bromine in organic synthesis is well-known. However, due to the hazardous nature of bromine, enormous growth has been witnessed in the past several decades for the development of solid bromine carriers. This review outlines the use of bromine and different bromo-organic compounds in organic synthesis. The applications of bromine, a total of 107 bromo-organic compounds, 11 other brominating agents, and a few natural bromine sources were incorporated. The scope of these reagents for various organic transformations such as bromination, cohalogenation, oxidation, cyclization, ring-opening reactions, substitution, rearrangement, hydrolysis, catalysis, etc. has been described briefly to highlight important aspects of the bromo-organic compounds in organic synthesis.

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Section: Rearrangement Reactionsmentioning

confidence: 99%

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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“…The traditional Hofmann rearrangement reaction requires stoichiometric amounts of bromine as a reagent, which limits its application in practical synthesis . Due to the wide application in the synthesis of natural products and biologically active compounds, alternative reagents have also been developed for the Hofmann rearrangement such as hypochlorites, N-bromosuccinimide (NBS), trichroloisocyanuric acid (TCCA), tribromoisocyanuric acid (TBCA), KBr, NaBr, difluorobromane, N-bromoacetamide (NBA), and others . Despite the recent development of Hofmann rearrangement promoted by continuous flow technology or electrochemistry, hypervalent iodine reagents still serve as environmentally friendly and efficient oxidants for this particular transformation.…”

Section: Introductionmentioning

confidence: 99%

Micelle-Enabled Hofmann Rearrangement in Water

Xing,

Zhao,

et al. 2024

Org. Process Res. Dev.

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An environmentally sustainable approach for the Hofmann rearrangement was developed. The presence of nanomicelles allows such a transformation to proceed smoothly in mild conditions with water as the sole reaction medium compared to traditional methods, which use significant amounts of organic solvents. A variety of amides containing functional groups have been constructed under these conditions, affording the compounding amine product in good to excellent yields (up to 99%). The process was scaled up and proven to be robust for its implementation in the synthesis of pharmaceutically relevant compounds.

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“…2 The classical Hofmann rearrangement involves the use of stoichiometric amounts of elemental bromine as a reagent. 3 Alternative reagents such as hypochlorites, 4 N-bromosuccinimide, 5 or tribromoisocyanuric acid 6 have also been reported. In all cases, precaution is needed during the scale-up of the process, given the use of highly reactive, corrosive, or toxic reagents.…”

Section: ■ Introductionmentioning

confidence: 99%

Multigram Electrochemical Hofmann Rearrangement Using a Spinning Three-Dimensional Anode

Malviya,

Bottecchia,

Stone

et al. 2023

Org. Process Res. Dev.

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A multigram electrochemical method for the Hofmann rearrangement of a primary amide into a methyl carbamate was developed using a spinning cylinder electrode cell. The method is based on the anodic oxidation of NaBr, an inexpensive and readily available bromide source, circumventing the use of stoichiometric amounts of oxidants. The multigram process relies on the use of a three-dimensional anode material, graphite felt, which has been implemented into the spinning cylinder electrode assembly. The felt material can efficiently oxidize the bromide salt by anodic oxidation, initiating the reaction. Additionally, the motion of the spinning three-dimensional electrode material provides excellent mass transfer to the system. The reaction was first optimized in a small-scale undivided beaker cell and then translated to a spinning electrode reactor. Improved productivity of the spinning cylinder technology was realized in a larger reactor with a 5-fold increase in the electrode surface area, providing analogous results to those obtained with the small cell. Under optimal conditions, high yields (95%) and productivity of 27 g of material per hour have been attained.

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TBCA mediated microwave-assisted Hofmann rearrangement

Cited by 12 publications

References 24 publications

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Micelle-Enabled Hofmann Rearrangement in Water

Multigram Electrochemical Hofmann Rearrangement Using a Spinning Three-Dimensional Anode

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