Chemoselective Reductions of Nitroaromatics in Water at Room Temperature

Kelly, Sean M.; Lipshutz, Bruce H.

doi:10.1021/ol403079x

Cited by 111 publications

(65 citation statements)

References 20 publications

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“…Considerable functional group tolerance was noted, and heteroaromatics rich in nitrogen (e.g., 16 and 17 ) appear to be amenable. The 2‐step sequence previously reported to arrive at procainamide could be significantly improved from both the overall efficiency standpoint as well as the environmental perspective using micellar catalysis (Scheme ) . The initial amide bond‐forming step could be done with EDCI–HOBt, followed by Zn‐mediated nitro group reduction, where the E Factors are over an order of magnitude lower than those of prior art…”

Section: Tandem/cascade Reactionsmentioning

confidence: 99%

The Hydrophobic Effect Applied to Organic Synthesis: Recent Synthetic Chemistry “in Water”

Lipshutz

Ghorai²,

Cortes‐Clerget

2018

Chemistry A European J

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296

182

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Recent developments over the past few years in aqueous micellar catalysis are discussed. Applications to problems in synthesis are highlighted, enabled by the use of surfactants that self-aggregate in water into micelles as nanoreactors. These include amphiphiles that have been available for some time, as well as those that have been newly designed. Reactions catalyzed by transition metals, including Pd, Cu, Rh, and Au, are of particular focus.

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Section: Tandem/cascade Reactionsmentioning

confidence: 99%

The Hydrophobic Effect Applied to Organic Synthesis: Recent Synthetic Chemistry “in Water”

Lipshutz

Ghorai²,

Cortes‐Clerget

2018

Chemistry A European J

Self Cite

296

182

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“…One solution very recently introduced relies on inexpensive zinc dust, out of the bottle, in water at room temperature. 29 Adding a substrate to water containing TPGS-750-M-derived nanomicelles in the presence of Zn dust leads to the virtually quantitative reduction of nitro groups (Scheme 5). The surfactant is crucial in this process, as the corresponding “on water” 30 alternative is not synthetically useful.…”

Section: New Technologies In Watermentioning

confidence: 99%

Transitioning organic synthesis from organic solvents to water. What's your E Factor?

Lipshutz

Ghorai²

2014

Green Chem.

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212

118

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Traditional organic chemistry, and organic synthesis in particular, relies heavily on organic solvents, as most reactions involve organic substrates and catalysts that tend to be water-insoluble. Unfortunately, organic solvents make up most of the organic waste created by the chemical enterprise, whether from academic, industrial, or governmental labs. One alternative to organic solvents follows the lead of Nature: water. To circumvent the solubility issues, newly engineered “designer” surfactants offer an opportunity to efficiently enable many of the commonly used transition metal-catalyzed and related reactions in organic synthesis to be run in water, and usually at ambient temperatures. This review focuses on recent progress in this area, where such amphiphiles spontaneously self-aggregate in water. The resulting micellar arrays serve as nanoreactors, obviating organic solvents as the reaction medium, while maximizing environmental benefits.

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“…The scope of this process has been studied in Pd‐catalysed coupling between: (i) alkyl halides and aryl or heteroaryl halides (Scheme ),79a,79f–79i (ii) alkyl or benzyl halides and alkenyl halides,79b,79e,79h and (iii) benzyl halides and aryl or heteroaryl halides 79c,79d. More recently, Lipshutz and co‐workers reported the reduction of alkyl halides81 and nitroaromatics82 in water and at room temperature with the aid of Zn dust in the presence of nanomicelles composed of the aforementioned surfactants.…”

Section: Organometallic Compounds Of D‐block Elementsmentioning

confidence: 99%

Reactivity of Polar Organometallic Compounds in Unconventional Reaction Media: Challenges and Opportunities

2015

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Developing new green solvents in designing chemical products and processes or successfully employing the already existing ones is one of the key subjects in green chemistry and is especially important in organometallic chemistry, which is an interdisciplinary field. Can we advantageously also use unconventional reaction media in place of current harsh organic solvents for polar organometallic compounds? This microreview critically analyses the state of the art with regard to this topic and showcases recent developments and breakthroughs that are becoming new research directions in this field. Because metals cover a vast swath of the Periodic Table the content is organized into three sections discussing the reactivity of organometallic compounds of s-, p- and d-block elements in unconventional solvents

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Chemoselective Reductions of Nitroaromatics in Water at Room Temperature

Cited by 111 publications

References 20 publications

The Hydrophobic Effect Applied to Organic Synthesis: Recent Synthetic Chemistry “in Water”

The Hydrophobic Effect Applied to Organic Synthesis: Recent Synthetic Chemistry “in Water”

Transitioning organic synthesis from organic solvents to water. What's your E Factor?

Reactivity of Polar Organometallic Compounds in Unconventional Reaction Media: Challenges and Opportunities

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