A chronicle of organic synthesis in water: A trajectory of growth in the intervening quarter century

Kitanosono, Taku; Yamashita, Yasuhiro; Kobayashi, Shū

doi:10.1016/j.tet.2023.133474

Tetrahedron

2023

DOI: 10.1016/j.tet.2023.133474

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A chronicle of organic synthesis in water: A trajectory of growth in the intervening quarter century

Taku Kitanosono

Yasuhiro Yamashita

Shū Kobayashi

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Cited by 7 publications

References 190 publications

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From Aldehyde to Ketone via Water‐Accelerated Molybdenum‐Photocatalysis

Meng,

Jia,

et al. 2024

ChemCatChem

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The efficient “on water” protocol was developed by employing molybdenum‐based polyoxometalate [N(C4H9)4]2[Mo6O19] as the photocatalyst. This water‐accelerated photoinduced process affords versatile ketones from aldehydes straightforwardly, showcasing exceptional substrate generality. Its applicability to life‐related molecules such as amino acids, peptides, and sugars, further demonstrates the bioorthogonal application. The mechanistic investigation highlights the hydrogen atom transfer (HAT) process between the excited‐state POM and benzaldehyde for acyl radical formation. Highly efficient gram‐scale flow operation underlines the industrial applicability of this transformative strategy.

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From Aldehyde to Ketone via Water‐Accelerated Molybdenum‐Photocatalysis

Meng,

Jia,

et al. 2024

ChemCatChem

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Recent Advances in Visible‐Light‐Driven Photocatalytic Oxidation Reactions in Water

Yang,

Wang,

Xie

2024

ChemSusChem

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Oxidation reactions, which represent a fundamental process in organic transformations, have consistently advanced over several decades. Owing to the widespread application of aqueous and photochemical synthesis, research on light‐induced oxidation in water, involving radical processes, has also experienced rapid development. Recently, numerous strategies for light‐induced aqueous oxidation have been ingeniously designed and developed. This review aims to discuss the notable recent advancements in this rapidly evolving field of oxidation reactions, with a focus on delving into the reaction mechanisms. It hopes to inspire the development of aqueous photocatalytic oxidation reactions.

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Asymmetric Allylation of Aldoxime Derivatives with β‐Amidoallylboronate in Water and Its Application to Divergent Synthesis of N‐Hydroxy‐γ‐Lactam and 1,2‐Oxazinan‐6‐one

Sengoku,

Anze,

Hasegawa

et al. 2024

ChemistrySelect

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A new application involving a water–stable amido–functionalized allylboronate has been developed for 1,2‐addition to carbon–nitrogen double bonds. The process achieves highly enantioselective allylation of aldoxime derivatives in water, by employing O‐Boc oximes as substrates under Zn(OH)2–chiral aminophenol catalysis. This process affords the corresponding homoallylic amines with 91–96 % ee. The products could be transformed into N‐hydroxy‐γ‐lactam or 1,2‐oxazinan‐6‐one, through an acidic or a protection‐acidic treatment sequence, respectively, almost without enantiopurity loss.

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A chronicle of organic synthesis in water: A trajectory of growth in the intervening quarter century

Cited by 7 publications

References 190 publications

From Aldehyde to Ketone via Water‐Accelerated Molybdenum‐Photocatalysis

From Aldehyde to Ketone via Water‐Accelerated Molybdenum‐Photocatalysis

Recent Advances in Visible‐Light‐Driven Photocatalytic Oxidation Reactions in Water

Asymmetric Allylation of Aldoxime Derivatives with β‐Amidoallylboronate in Water and Its Application to Divergent Synthesis of N‐Hydroxy‐γ‐Lactam and 1,2‐Oxazinan‐6‐one

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