trans-Hydroboration–oxidation products in Δ5-steroids via a hydroboration-retro-hydroboration mechanism

Hilario-Martínez, J. Ciciolil; Murillo, Fernando; García-Méndez, Jair; Dzib, Eugenia; Sandoval‐Ramírez, Jesús; Muñoz‐Hernández, Miguel‐Ángel; Bernès, Syl­vain; Kürti, László; Duarte, Fernanda; Merino, Gabriel; Fernández-Herrera, María A.

doi:10.1039/d0sc01701a

Chem. Sci.

2020

DOI: 10.1039/d0sc01701a

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trans-Hydroboration–oxidation products in Δ⁵-steroids via a hydroboration-retro-hydroboration mechanism

J. Ciciolil Hilario-Martínez

Fernando Murillo

Jair García-Méndez

et al.

Abstract: Herein, we report for the first time a “trans-hydroboration-oxidation product” isolated and characterized under traditional hydroboration-oxidation conditions using cholesterol and diosgenin as substrates, which are excellent starting materials because of...

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Chromium‐Doped Nickel Oxide and Nickel Nitride Mediate Selective Electrocatalytic Oxidation of Sterol Intermediates Coupled with H₂ Evolution

Li,

Wang,

et al. 2023

Angewandte Chemie

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Replacing the oxygen evolution reaction (OER) with the thermodynamically favorable electrooxidation of organics is considered a promising approach for the simultaneous production of hydrogen (H 2 ) and high-value chemicals. However, exploring and optimizing efficient electrocatalysts remains a challenge for large-scale production of valueadded steroid carbonyl and H 2 . Herein, Cr-NiO/GF and Cr-Ni 3 N/GF (GF: graphite felt) electrocatalysts were designed as anode and cathode for the production of steroid carbonyls and H 2 , respectively. The cooperative Cr-NiO and ACT (4acetamido-2,2,6,6-tetramethyl-1-piperidine-N-oxyl) electrocatalyst can be extended to the electrooxidation of a series of steroid alcohols to the corresponding aldehydes. Additionally, Cr-Ni 3 N displays superior electrocatalytic activity for hydrogen evolution reaction (HER), with a low overpotential of 35 mV to deliver 10 mA cm À 2 . Furthermore, the system coupled with anodic electrooxidation of sterol and cathodic HER exhibited excellent performance with high space-time yield of 48.85 kg m À 3 h À 1 for steroid carbonyl and 1.82 L h À 1 for H 2 generation in a two-layer stacked flow cell. Density Functional Theory (DFT) calculations indicated that Cr doping effectively stabilizes ACTH on the NiO surface, and ACTH molecule could be captured via the ketonic oxygen interaction with Cr, resulting in excellent electrocatalytic activity. This work develops a novel approach to the rational design of efficient electrocatalysts for the simultaneous production of H 2 and large-scale value-added pharmaceutical carbonyl intermediates.

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Chromium‐Doped Nickel Oxide and Nickel Nitride Mediate Selective Electrocatalytic Oxidation of Sterol Intermediates Coupled with H₂ Evolution

Li,

Wang,

et al. 2023

Angewandte Chemie

View full text Add to dashboard Cite

show abstract

Chromium‐Doped Nickel Oxide and Nickel Nitride Mediate Selective Electrocatalytic Oxidation of Sterol Intermediates Coupled with H₂ Evolution

Li,

Wang,

et al. 2023

Angew Chem Int Ed

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Synthesis and biological in vitro evaluation of the effect of hydroxyimino steroidal derivatives on breast cancer cells

et al. 2021

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trans-Hydroboration–oxidation products in Δ⁵-steroids via a hydroboration-retro-hydroboration mechanism

Abstract: Herein, we report for the first time a “trans-hydroboration-oxidation product” isolated and characterized under traditional hydroboration-oxidation conditions using cholesterol and diosgenin as substrates, which are excellent starting materials because of...

Cited by 5 publications

References 25 publications

Chromium‐Doped Nickel Oxide and Nickel Nitride Mediate Selective Electrocatalytic Oxidation of Sterol Intermediates Coupled with H₂ Evolution

Chromium‐Doped Nickel Oxide and Nickel Nitride Mediate Selective Electrocatalytic Oxidation of Sterol Intermediates Coupled with H₂ Evolution

Chromium‐Doped Nickel Oxide and Nickel Nitride Mediate Selective Electrocatalytic Oxidation of Sterol Intermediates Coupled with H₂ Evolution

Synthesis and biological in vitro evaluation of the effect of hydroxyimino steroidal derivatives on breast cancer cells

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trans-Hydroboration–oxidation products in Δ5-steroids via a hydroboration-retro-hydroboration mechanism

Abstract: Herein, we report for the first time a “trans-hydroboration-oxidation product” isolated and characterized under traditional hydroboration-oxidation conditions using cholesterol and diosgenin as substrates, which are excellent starting materials because of...

Cited by 5 publications

References 25 publications

Chromium‐Doped Nickel Oxide and Nickel Nitride Mediate Selective Electrocatalytic Oxidation of Sterol Intermediates Coupled with H2 Evolution

Chromium‐Doped Nickel Oxide and Nickel Nitride Mediate Selective Electrocatalytic Oxidation of Sterol Intermediates Coupled with H2 Evolution

Chromium‐Doped Nickel Oxide and Nickel Nitride Mediate Selective Electrocatalytic Oxidation of Sterol Intermediates Coupled with H2 Evolution

Synthesis and biological in vitro evaluation of the effect of hydroxyimino steroidal derivatives on breast cancer cells

Contact Info

Product

Resources

About

trans-Hydroboration–oxidation products in Δ⁵-steroids via a hydroboration-retro-hydroboration mechanism

Chromium‐Doped Nickel Oxide and Nickel Nitride Mediate Selective Electrocatalytic Oxidation of Sterol Intermediates Coupled with H₂ Evolution

Chromium‐Doped Nickel Oxide and Nickel Nitride Mediate Selective Electrocatalytic Oxidation of Sterol Intermediates Coupled with H₂ Evolution

Chromium‐Doped Nickel Oxide and Nickel Nitride Mediate Selective Electrocatalytic Oxidation of Sterol Intermediates Coupled with H₂ Evolution