A Practical solution for aqueous reactions of water-insoluble high-melting-point organic substrates

Cui, Xiaoxue; Li, Bo; Liu, Tianzhen; Li, Chunbao

doi:10.1039/c2gc16328d

Cited by 18 publications

(20 citation statements)

References 9 publications

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“…Although other VSSHMP substrates have been used in reactions mediated by water, they are often bis-or triphasic and metal reagents have not been used as the solid phase. 20,21,29,30 In this aqueous system, water and Aliquat 336 may facilitate the electron transfer from the solid zinc to the iodosteroid. Therefore, the aqueous reduction is faster and higher yielding than reductions mediated by organic solvents.…”

Section: Resultsmentioning

confidence: 99%

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Aqueous Reduction of Iodosteroids to Deoxysteroids

Liu

Sun

2014

Journal of Chemical Research

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A new method for the reduction of iodosteroids to deoxysteroids has been developed using Zn, HCOOH and a catalytic amount of Aliquat 336 in water. In total, 13 iodosteroids were reduced in good to excellent yields. The higher solubilities of the substrates lead to the faster reactions, and the aqueous reaction was efficiently accelerated by granular polytetrafluoroethylene. The advantage of the aqueous system over eight organic solvents has also been demonstrated.

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Section: Resultsmentioning

confidence: 99%

“…In previous research, we have carried out a series of aqueous organic reactions of VSSHMP compounds in the presence of granular PTFE and a catalytic amount of Aliquat 336. 20,21 We now report a methodology for the conversion of iodosteroids to deoxysteroids mediated by water in the presence of granular PTFE and a catalytic amount of Aliquat 336.…”

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confidence: 99%

Aqueous Reduction of Iodosteroids to Deoxysteroids

Liu

Sun

2014

Journal of Chemical Research

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“…The reaction proceeded smoothly with hydroxylamine and phenyl hydrazine respectively to afford 77 and 78 in nearly quantitative yields (Scheme 31). 36,67 Condensations of 1 with other aromatic amines and hydrazines produced imine and hydrazone derivatives with yields of ≥81%. 62 fonamides 79a-b by the stereoselective reductions of imine and enol ether with Pd/C and subsequent reactions of amines with sulfonyl chlorides (Scheme 31).…”

Section: The Modifications Of Enone Of Sinomenine (C-ring)mentioning

confidence: 99%

The present and future synthetic strategies of structural modifications of sinomenine

Coghi

Law

et al. 2020

Org. Chem. Front.

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“…In this system, Aliquat 336 works as both catalyst and solvent, and its efficiency is enhanced by the moving sand under mechanical stirring. This mixture was successfully applied in the good-yield oxidation of pseudosapogenins into 16-dehydropregnenolone acetate and its analogues using H 2 O 2 and catalyzed by V 2 O 5 [106]. This transformation is of high impact because 16-dehydropregnenolone acetate and similar compounds are important starting materials for the preparation of several semisynthetic steroid drugs [2].…”

Section: Green Nanotechnology -Overview and Further Prospectsmentioning

confidence: 99%

Recent Highlights in Green Oxidative Chemical Processes Applied to Steroid Chemistry

Silvestre¹,

Silva²,

Salvador³

2016

Green Nanotechnology - Overview and Further Prospects

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Steroids and their oxidation products are widely distributed in living organisms and are important intermediates for the synthesis of many biologically active molecules. Due to their pharmacological and synthetic relevance, several oxidative chemical processes for the functionalization of the steroid nucleus have been developed. Green chemistry principles have been incorporated in some oxidative transformations of steroids, allowing significant advances in synthetic chemistry applied to these compounds. This chapter presents a selection of relevant applications of pharmaceutical green chemistry to steroid's oxidative processes. Special emphasis is given to catalytic processes encompassing heterogeneous nanocatalysts, whose application in this context is increasing over the past years. This chapter is organized according to the reaction type that includes alcohol oxidation, epoxidation of alkenes, and allylic oxidation of alkenes to enones, among other relevant oxidative transformations. Biocatalytic oxidative methods applied to steroid synthesis are not included in this review.

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A Practical solution for aqueous reactions of water-insoluble high-melting-point organic substrates

Cited by 18 publications

References 9 publications

Aqueous Reduction of Iodosteroids to Deoxysteroids

Aqueous Reduction of Iodosteroids to Deoxysteroids

The present and future synthetic strategies of structural modifications of sinomenine

Recent Highlights in Green Oxidative Chemical Processes Applied to Steroid Chemistry

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