Access to α‐Amino Acid Esters through Palladium‐Catalyzed Oxidative Amination of Vinyl Ethers with Hydrogen Peroxide as the Oxidant and Oxygen Source

Ouyang, Lu; Li, Jianxiao; Zheng, Jia; Huang, Jiuzhong; Qi, Chaorong; Wu, Wanqing; Jiang, Huanfeng

doi:10.1002/anie.201709285

Cited by 56 publications

(24 citation statements)

References 60 publications

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“…Simultaneously, our research also extended to another green oxidant: H 2 O 2 . In 2017, we demonstrated a highly innovative and convenient palladium‐catalyzed oxidative amination of amines with vinyl esters, and plentiful functionalized α‐amino acid esters (Scheme ) . Notably, 18 O‐labeling experiments suggested that H 2 O 2 acted as a green oxidant and oxygen source (Scheme ).…”

Section: H2o2 or Tbhp As The Oxidantmentioning

confidence: 99%

“… Proposed catalytic cycle for the palladium‐catalyzed oxidative amination of amines with vinyl esters …”

Section: H2o2 or Tbhp As The Oxidantmentioning

confidence: 99%

“…[58] ChemSusChem 2019, 12, www.chemsuschem.org and convenient palladium-catalyzed oxidative amination of amines with vinyl esters, and plentiful functionalized a-amino acid esters (Scheme49). [68] Notably, 18 O-labeling experiments suggested that H 2 O 2 acted as ag reen oxidanta nd oxygen source (Scheme 50).…”

Section: Minireviewsmentioning

confidence: 99%

“…Selectede xamples of a-amino acid esters. [68] ChemSusChem 2019, 12, www.chemsuschem.org 2019 Wiley-VCH Verlag GmbH &Co. KGaA, Weinheim 2932 Minireviews Scheme51. Proposed catalytic cycle for the palladium-catalyzed oxidative amination of amines with vinyl esters.…”

Section: Minireviewsmentioning

confidence: 99%

“…Proposed catalytic cycle for the palladium-catalyzed oxidative amination of amines with vinyl esters. [68] Scheme52. Proposed catalytic cycle for the palladium-catalyzed dioxygenation of alkenes.…”

Section: Minireviewsmentioning

confidence: 99%

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Palladium‐Catalyzed Oxidation Reactions of Alkenes with Green Oxidants

Jiang

2019

ChemSusChem

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Transition‐metal‐catalyzed oxidative functionalization of alkenes has emerged as a powerful and valuable tool in modern organic synthesis. Recently, many methods have been established for the assembly of C−C and C–heteroatom bonds, which provides tremendous possibility for application in biology, medicine, and materials science. However, the use of stoichiometric amounts of strong oxidants leads to poor selectivity, low atom economy, and a series of undesired waste products. By contrast, green oxidants, such as O2, H2O2, or tert‐butyl hydroperoxide (TBHP), have bright prospects due to their attributes of mild, low cost, and great sustainability in transition‐metal‐catalyzed oxidation reactions. Based on the great and unique potential for the development of aerobic reactions, this review mainly highlights homogenous palladium‐catalyzed green oxidations of alkenes that have been reported in recent years. These methods provide new strategies for the transformation and functionalization of alkenes; some of them have also been successfully applied to the synthesis of the core structures of drugs and natural products. Additionally, through in‐depth studies of the reaction mechanisms in this field, it is believed that palladium‐catalyzed green oxidation reactions of alkenes with O2, H2O2, or TBHP will create added value for organic synthetic chemistry.

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Section: H2o2 or Tbhp As The Oxidantmentioning

confidence: 99%

“… Proposed catalytic cycle for the palladium‐catalyzed oxidative amination of amines with vinyl esters …”

Section: H2o2 or Tbhp As The Oxidantmentioning

confidence: 99%

Section: Minireviewsmentioning

confidence: 99%

Section: Minireviewsmentioning

confidence: 99%

Section: Minireviewsmentioning

confidence: 99%

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Palladium‐Catalyzed Oxidation Reactions of Alkenes with Green Oxidants

Jiang

2019

ChemSusChem

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Iodine‐Catalyzed Oxidative Rearrangement of Amines to α‐Amino Acetals and α‐Amino Aldehydes

2019

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Transition‐Metal‐Free Three‐Component Synthesis of Tertiary Aryl Amines from Nitro Compounds, Boronic Acids, and Trialkyl Phosphites

Roscales

Csákÿ

2019

Adv Synth Catal

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The synthesis of aromatic amines is of continuous interest in chemistry. An exceptionally versatile three‐component reaction that directly transforms inexpensive nitro compounds, boronic acids, and trialkyl phosphites into tertiary aromatic amines has been realized. The reaction tolerates alkyl and aryl substituents on the nitro and boronic acid moieties, as well as functionalized phosphites. No transition‐metal catalysis is required. The method is orthogonal to other classical metal‐catalyzed syntheses since it tolerates the presence of halogens, and also permits the synthesis of functionalized compounds such as α‐amino ester derivatives.

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Access to α‐Amino Acid Esters through Palladium‐Catalyzed Oxidative Amination of Vinyl Ethers with Hydrogen Peroxide as the Oxidant and Oxygen Source

Cited by 56 publications

References 60 publications

Palladium‐Catalyzed Oxidation Reactions of Alkenes with Green Oxidants

Palladium‐Catalyzed Oxidation Reactions of Alkenes with Green Oxidants

Iodine‐Catalyzed Oxidative Rearrangement of Amines to α‐Amino Acetals and α‐Amino Aldehydes

Transition‐Metal‐Free Three‐Component Synthesis of Tertiary Aryl Amines from Nitro Compounds, Boronic Acids, and Trialkyl Phosphites

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