An efficient Julia olefination mediated by magnesium in ethanol

Lee, Ge Hyeong; Lee, Hyeon Kyu; Choi, Eun Bok; Kim, Bum Tae; Pak, Chwang Siek

doi:10.1016/0040-4039(95)01073-q

Cited by 34 publications

(21 citation statements)

References 8 publications

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“…Since then, the combination SmI 2 /HMPA or SmI 2 and various additives [105] has continued to prove its usefulness [106][107][108]. In addition, other reductive methods are regularly reported, such as the use of Mg/HgCl 2 [109,110], NaTeH [111], and sulfoxide/alkyllithium [52,53] combinations.…”

Section: Reductive Eliminationmentioning

confidence: 99%

The Julia Reaction

Dumeunier

Markó

2003

Modern Carbonyl Olefination

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Section: Reductive Eliminationmentioning

confidence: 99%

The Julia Reaction

Dumeunier

Markó

2003

Modern Carbonyl Olefination

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“…This result is remarkable because sulfones are typically inert under reductive conditions or they undergo C–S bond cleavage to sulfites . Reductions of sulfones to sulfides are rare, and they require strong reducing agents (e.g., SmI 2 or Mg/MeOH) .…”

Section: Resultsmentioning

confidence: 99%

Rapid and Chemodivergent Synthesis of N-Heterocyclic Sulfones and Sulfides: Mechanistic and Computational Details of the Persulfate-Initiated Catalysis

et al. 2019

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N-Heterocyclic sulfones and sulfides are key functional motifs in medicinal and agricultural chemistry and important building blocks in organic synthesis. Currently available methods produce N-heterocyclic sulfones in low yields and under harsh conditions. Here, we describe a rapid sulfone synthesis under ambient conditions that is initiated by persulfate with water as a cosolvent. The reaction has a broad scope and is readily expanded to the chemodivergent synthesis of symmetrical N-heterocyclic sulfones and sulfides. The products can be isolated by simple filtration. Our combined experimental and computational study suggests that the remarkable persulfate-initiated acceleration of the sulfone formation in the biphasic system that enables the otherwise sluggish reaction under ambient conditions is due to the combination of the previously unknown rapid acidification of the persulfate–sulfinate system, the self-catalysis of the reaction of sulfinic acid with halo-N-heterocycles, and the substantial acceleration of the reaction in the aqueous phase.

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“…Mg (OMe) 2 + H 2 There after its use has been expanded not only to the selective reduction of various functional groups, but also to the reduction of conjugated double and triple bonds tethered to diverse functional groups such as esters [6], nitriles [7], amides [8] and aromatics [9] to the corresponding saturated analogs. Mg/MeOH has been demonstrated as a convenient single electron transfer reagent for a number of reductive reactions [10].…”

Section: Introductionmentioning

confidence: 99%

Palladium/Carbon Catalyzed Hydrogen Transfer Reactions using Magnesium/Water as Hydrogen Donor

et al. 2008

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A new methodology is developed for the hydrogenation reaction using magnesium/water system, as hydrogen source under catalytic palladium on activated carbon (Pd/C). The method is highly efficient for the chemoselective reduction of wide range of unsaturated aldehydes and ketones. The process is also found to be suitable when we think about green chemistry for the ecofriendly hydro-dehalogenation of aromatics. From practical point of view this new methodology is the most attractive, efficient, economical and convenient approach towards industrially important reduction transformations. This report is intended to highlight the use of Mg/H 2 O system in these organic transformations which can be easily adopted in industrial scale for the bulk production of hydrogenation products.

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An efficient Julia olefination mediated by magnesium in ethanol

Cited by 34 publications

References 8 publications

The Julia Reaction

The Julia Reaction

Rapid and Chemodivergent Synthesis of N-Heterocyclic Sulfones and Sulfides: Mechanistic and Computational Details of the Persulfate-Initiated Catalysis

Palladium/Carbon Catalyzed Hydrogen Transfer Reactions using Magnesium/Water as Hydrogen Donor

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