Catalytic and supported Barton–McCombie deoxygenation of secondary alcohols: a clean reaction

Boussaguet, Paul; Delmond, B.; Dumartin, Gilles; Pereyre, Michel

doi:10.1016/s0040-4039(00)00418-4

Cited by 34 publications

(6 citation statements)

References 11 publications

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“…In addition to the reduction of organic halides, which is the usual test experiment for an evaluation of the grafted reagent quality, , these supported tin hydrides can also be used in the hydrostannylation of alkynes − or in the Barton–McCombie deoxygenation of alcohols . In the latter case, a catalytic variant was reported using hydrogenosilanes for the inside regeneration of the tin hydride.…”

Section: Reagents or Substrates Grafted On Organic Or Inorganic Matrixesmentioning

confidence: 95%

Methodologies Limiting or Avoiding Contamination by Organotin Residues in Organic Synthesis

et al. 2015

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Section: Reagents or Substrates Grafted On Organic Or Inorganic Matrixesmentioning

confidence: 95%

Methodologies Limiting or Avoiding Contamination by Organotin Residues in Organic Synthesis

et al. 2015

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“…Dumartin’s group [ 61 ] investigated the possibility to use tin-based reducing agent in catalytic amount, as it had been done in solution [ 62 ]. In particular, their attention focused on the use of siloxanes, particularly polymethylhydrosiloxane (PMHS), for the regeneration of catalytic amounts of TBTH.…”

Section: Solid-supported Reagents Resins and Linkersmentioning

confidence: 99%

From Polymer to Small Organic Molecules: A Tight Relationship between Radical Chemistry and Solid-Phase Organic Synthesis

Mirizzi

Pulici

2011

Molecules

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Since Gomberg’s discovery of radicals as chemical entities, the interest around them has increased through the years. Nowadays, radical chemistry is used in the synthesis of 75% of all polymers, inevitably establishing a close relationship with Solid-Phase Organic Synthesis. More recently, the interest of organic chemists has shifted towards the application of usual “in-solution” radical chemistry to the solid-phase, ranging from the use of supported reagents for radical reactions, to the development of methodologies for the synthesis of small molecules or potential libraries. The aim of this review is to put in perspective radical chemistry, moving it away from its origin as a synthetic means for solid supports, to becoming a useful tool for the synthesis of small molecules.

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“…and colleagues illustrated the addition of trimethyl silane can reduce the contamination of toxic tin byproducts. [12] Nishiyama. et al (Figure 1c) discovered that when using rhenium complexes such as ReBr(CO) 5 and triphenyl silane, as catalysts, the reduction reaction occurred and the corresponding deoxidized alkanes were generated.…”

Section: Introductionmentioning

confidence: 99%

Brønsted‐Acidic Mesoporous Beta Zeolite H‐MBeta Catalyzes the Conversion of Benzhydrol into Diphenylmethane and Diphenyl Ketone

Jia,

Geng,

Wang

et al. 2024

ChemistrySelect

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Developing a highly efficient catalytic system for the transformation of benzhydrol to simultaneously form diphenylmethane and diphenyl ketone is an attractive strategy in modern organic synthesis. In this work, acidic mesoporous Beta (H‐MBeta) zeolite successfully catalyzed the dismutation of the benzhydrol to yield equivalent amounts of diphenylmethane and diphenyl ketone under mild conditions. Combining X‐ray diffraction, N2‐adsorption, ammonia temperature programmed desorption, pyridine‐adsorbed infrared spectra, scanning electron microscopy and transmission electron microscopy, it was found that, compared to MBeta, H‐MZSM‐5 and USY zeolite catalysts, the abundant Brønsted acidic sites on the external surface of H‐MBeta are responsible for its superior catalytic performance.

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Catalytic and supported Barton–McCombie deoxygenation of secondary alcohols: a clean reaction

Cited by 34 publications

References 11 publications

Methodologies Limiting or Avoiding Contamination by Organotin Residues in Organic Synthesis

Methodologies Limiting or Avoiding Contamination by Organotin Residues in Organic Synthesis

From Polymer to Small Organic Molecules: A Tight Relationship between Radical Chemistry and Solid-Phase Organic Synthesis

Brønsted‐Acidic Mesoporous Beta Zeolite H‐MBeta Catalyzes the Conversion of Benzhydrol into Diphenylmethane and Diphenyl Ketone

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