Catalytic Oxidative Processes in Steroid Chemistry: Allylic Oxidation, &amp;#946;-Selective Epoxidation, Alcohol Oxidation and Remote Functionalization Reactions

Salvador, Jorge A. R.; Silvestre, Samuel; Moreira, Vânia M.

doi:10.2174/138527206778742641

Cited by 47 publications

(9 citation statements)

References 142 publications

(160 reference statements)

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“…To the best of our knowledge, currently there is no metal-free catalyst known for the oxidation of steroids using oxygen as the oxidant. In most of the cases, stoichiometric oxidants and/or metal-based catalysts have been used. − Therefore, because of the interest of pharmaceutical companies, this catalyst can find strong interest in steroid chemistry.…”

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confidence: 98%

Metal-Free Catalyst for Visible-Light-Induced Oxidation of Unactivated Alcohols Using Air/Oxygen as an Oxidant

et al. 2018

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9-Fluorenone acts as a metal-free and additive-free photocatalyst for the selective oxidation of primary and secondary alcohols under visible light. With this photocatalyst, a plethora of alcohols such as aliphatic, heteroaromatic, aromatic, and alicyclic compounds has been converted to the corresponding carbonyl compounds using air/oxygen as an oxidant. In addition to these, several steroids have been oxidized to the corresponding carbonyl compounds. Detailed mechanistic studies have also been achieved to determine the role of the oxidant and the photocatalyst for this oxidation.

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confidence: 98%

Metal-Free Catalyst for Visible-Light-Induced Oxidation of Unactivated Alcohols Using Air/Oxygen as an Oxidant

et al. 2018

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“…To get further information about the reaction mechanism, Stern–Volmer quenching experiments were carried out (see Figure ). The excited state of the photocatalyst was quenched by 1-benzylpiperidine . As shown in Figure , a clear decrease of light emission was observed with the increase of substrate concentration, and no change was observed in the case of a solution saturated with oxygen.…”

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confidence: 90%

Visible-Light-Mediated Efficient Metal-Free Catalyst for α-Oxygenation of Tertiary Amines to Amides

et al. 2018

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A metal-free system has been discovered for the efficient α-oxygenation of tertiary amines to the corresponding amides using oxygen as an oxidant. This visible-light-mediated oxygenation reaction exhibited excellent substrates scope under mild reaction conditions and generated water as the only byproduct. The synthetic utility of this approach has been demonstrated by applying onto drug molecules. At the end, detailed mechanistic reactions clearly showed the role of oxygen and the photocatalyst.

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“…Environmental and health concerns have motivated the search for new oxidants and catalysts [18]. From chromium based catalysts, the next phase in steroidal allylic oxidation manifested through more environmentally friendly metallic catalysts that use TBHP as an oxygen donor.…”

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confidence: 99%

A Short Review of Methods for the Allylic Oxidation of Δ5 Steroidal Compounds to Enones

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2016

J Steroids Horm Sci

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Introduction of α, β-unsaturated ketones to ∆ 5 steroidal olefins changes the characteristics and biological function of those compounds. Several synthetic methods have been reported to accomplish carbonyl introduction to ∆ 5 steroidal olefins. Herein, this short review will catalogue many of those oxidative methods, particularly those proceeding through a peroxide intermediate and/or use chromium complexes as reagents. to undesired side products, one in particular being C25 for steroids with side chains [15]. Furthermore, cleavage of the side chain can occur concurrent with allylic oxidation [16].Protecting the C3 hydroxy group is commonly accomplish by esterification using acetic anhydride to make cholesteryl acetate. The authors of this review prefer esterification with benzoyl chloride since cholesteryl benzoate products can be more easily isolated with recrystallization in acetone and water than the steroidal acetates. This esterification is necessary because many oxidants and catalysts will convert the C3 hydroxyl group to a ketone [17].Due to interest in "green" or environmentally benign chemistry, chemists have questioned the ethics of earlier catalysts. Environmental and health concerns have motivated the search for new oxidants and catalysts [18]. From chromium based catalysts, the next phase in steroidal allylic oxidation manifested through more environmentally friendly metallic catalysts that use TBHP as an oxygen donor. Meanwhile, several methods have been reported to give steroidal oxidation without any metal catalysts using as sodium chlorite and sodium hypochlorite [19,20]. Additionally, recoverable heterogeneous catalysts, clay

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Catalytic Oxidative Processes in Steroid Chemistry: Allylic Oxidation, β-Selective Epoxidation, Alcohol Oxidation and Remote Functionalization Reactions

Cited by 47 publications

References 142 publications

Metal-Free Catalyst for Visible-Light-Induced Oxidation of Unactivated Alcohols Using Air/Oxygen as an Oxidant

Metal-Free Catalyst for Visible-Light-Induced Oxidation of Unactivated Alcohols Using Air/Oxygen as an Oxidant

Visible-Light-Mediated Efficient Metal-Free Catalyst for α-Oxygenation of Tertiary Amines to Amides

A Short Review of Methods for the Allylic Oxidation of Δ5 Steroidal Compounds to Enones

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