Remarkable reactivity of pyridinium chlorochromate adsorbed on neutral alumina under solvent-free conditions

Bhar, Sanjay; Chaudhuri, Subrata Kumar

doi:10.1016/s0040-4020(03)00471-x

Cited by 24 publications

(6 citation statements)

References 18 publications

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“…The system CS-LiBr, unlike CAN-LiBr, does not oxidize alkanols in the absence of a solvent; even when reagents are in contact for 72 h, conversion of the alkanol is very low (see Table 1, entries 1-3). A positive result was easily achieved in aqueous solution: at 20 °C with the reaction time being ~8 h, and the ratio of reagents 1b : CS : LiBr equal to 1 : 4 : 3, the conversion of this alcohol and the yield of heptyl heptanoate (2b) 21 were almost quantitative (entry 19). In the absence of LiBr, heptan 1 ol 1b remains virtually unchanged (entries 7, 9, and 10), though for the 24 h contact of the reagents at 20 °C, CS is completely consumed.…”

Section: Methodsmentioning

confidence: 99%

Oxidation of alkanols into “symmetric” esters with the system Ce(SO4)2—LiBr

2009

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Section: Methodsmentioning

confidence: 99%

Oxidation of alkanols into “symmetric” esters with the system Ce(SO4)2—LiBr

2009

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“…To date, various reaction systems have been developed, which include stoichiometric oxidation using Na 2 Cr 2 O 7 , 3 Br 2 -HMPT, 4 Ca(OCl) 2 , 5 NaOCl, 5 NaBrO 2 , 6 NaBrO 3 -NaHSO 3 , 7 PCC-Al 2 O 3 , 8 and so on. Recently, Bobbitt et al reported oxidative dimerization of polyfunctional primary alcohols using oxoammonium salts.…”

Section: Methodsmentioning

confidence: 99%

“…Moreover, except for the Shvo 12 and Murahashi 13 methods, benzyl alcohols are usually difficult substrates for oxidative dimerization by catalytic or stoichiometric methods, and the major products are not the dimeric esters, but benzaldehydes. 4,5,7,8,11,14 Thus, an efficient oxidative dimerization with broad generality has not yet been developed.…”

Section: Methodsmentioning

confidence: 99%

Iridium-Catalyzed Oxidative Dimerization of Primary Alcohols to Esters Using 2-Butanone as an Oxidant

Suzuki¹,

Matsuo²,

Watanabe³

et al. 2005

Synlett

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I r i d i u m -C a t a l y z e d O x i d a t i v e D i m e r i z a t i o n o f P r i m a r y A l c o h o l s t o E s t e r sAbstract: Oxidative dimerization of primary alcohols with 2-butanone in the presence of an amino alcohol-based Ir bifunctional catalyst was accomplished for the first time. The reaction proceeds with 1-2 mol% of the catalyst and 0.3 mol equivalents of K 2 CO 3 in 2-butanone at room temperature to give the corresponding dimeric esters in 30-93% yield.

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“…Of these, reaction A proceeds with the assistance of an acid catalyst, [4,5] and reaction B typically proceeds in the presence of a transition metal catalyst suitable for the dehydrogenative transformation of organic molecules. [6][7][8][9][10][11][12][13] To date, many researchers have reported dehydrogenative esterification reactions using a variety of transition metal catalysts. [6][7][8][9][10][11][12][13] Esters and ethers, the products in Scheme 1, are a significant class of compounds, ranging from industrial largescale synthesis to lab-level small-scale synthesis.…”

Section: Introductionmentioning

confidence: 99%

Dehydrogenative Esterification and Dehydrative Etherification by Coupling of Primary Alcohols Based on Catalytic Function Switching of an Iridium Complex

Onoda

Fujita

2022

ChemistrySelect

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Esters and ethers are widely used in modern organic synthesis. In recent years, the synthesis of esters by the dehydrogenative coupling of primary alcohols has been reported to be an environmentally benign process. In this situations, if a single catalyst can be used for the synthesis of either esters or ethers by making slight alterations to the reaction conditions, the value of the synthetic methodology would increase. In this study, we successfully developed a new catalytic function switching system: not only dehydrogenative esterification but also dehydrative etherification under environmentally friendly conditions were accomplished by the employment of a single iridium catalyst based on catalytic function switching. Using benzyl alcohol as a starting material, the esterification product, benzyl benzoate, and the etherification product, dibenzyl ether, were obtained in 92 % and 89 % yields, respectively, by employing same iridium catalyst precursor bearing a dihydroxybipyridine ligand, under optimized conditions.

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Remarkable reactivity of pyridinium chlorochromate adsorbed on neutral alumina under solvent-free conditions

Cited by 24 publications

References 18 publications

Oxidation of alkanols into “symmetric” esters with the system Ce(SO4)2—LiBr

Oxidation of alkanols into “symmetric” esters with the system Ce(SO4)2—LiBr

Iridium-Catalyzed Oxidative Dimerization of Primary Alcohols to Esters Using 2-Butanone as an Oxidant

Dehydrogenative Esterification and Dehydrative Etherification by Coupling of Primary Alcohols Based on Catalytic Function Switching of an Iridium Complex

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