Cu<sup>II</sup>/TEMPO‐Catalyzed Enantioselective C(sp<sup>3</sup>)–H Alkynylation of Tertiary Cyclic Amines through Shono‐Type Oxidation

Gao, Pei‐Sen; Weng, Xin‐Jun; Wang, Zhen‐Hua; Zheng, Chao; Sun, Bing; Chen, Zhi‐Hao; You, Shu‐Li; Mei, Tian‐Sheng

doi:10.1002/ange.202005099

Cited by 28 publications

(1 citation statement)

References 92 publications

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“…In 2020, Mei and co‐workers developed a protocol of copper‐electrocatalyzed and TEMPO mediated asymmetric Shono‐type oxidative cross‐coupling providing C1‐alkynylated tetrahydroisoquinolines (THIQs) in good to excellent enantioselectivities [103] . Generality of the method was probed by substitution on THIQs in optimized conditions.…”

Section: Copper‐electrocatalyzed Alkynylationmentioning

confidence: 99%

Transition Metal‐Catalyzed C−H Functionalization Through Electrocatalysis

et al. 2023

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Electrochemically promoted transition metal‐catalyzed C−H functionalization has emerged as a promising area of research over the last few decades. However, development in this field is still at an early stage compared to traditional functionalization reactions using chemical‐based oxidizing agents. Recent reports have shown increased attention on electrochemically promoted metal‐catalyzed C−H functionalization. From the standpoint of sustainability, environmental friendliness, and cost effectiveness, electrochemically promoted oxidation of a metal catalyst offers a mild, efficient, and atom‐economical alternative to traditional chemical oxidants. This Review discusses advances in the field of transition metal‐electrocatalyzed C−H functionalization over the past decade and describes how the unique features of electricity enable metal‐catalyzed C−H functionalization in an economic and sustainable way.

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Section: Copper‐electrocatalyzed Alkynylationmentioning

confidence: 99%

Transition Metal‐Catalyzed C−H Functionalization Through Electrocatalysis

et al. 2023

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Emerging Strategies for Asymmetric Synthesis: Combining Enzyme Promiscuity and Photo‐/Electro‐redox Catalysis

Long

Guan

2023

Asian J Org Chem

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As an emerging opportunity to expand the reactivity repertoire of enzymes to achieve unnatural transformations of enzymes in organic synthesis, enzyme promiscuity has attracted great interest in recent years. The combination of enzyme catalysis and photo-/electro-redox catalysis which can benefit from both the exquisite selectivity of enzymes and unique chemical transformations accessible to photo-/electro-chemistry has many advantages, such as new reactivity, high enantioselectivity, green synthesis, and high yields. In the past decades, most photoenzymatic catalysis and enzymatic electrosynthesis mainly focused on exploiting regenerated cofactors to function in native enzymatic activity. However, recent developments have demonstrated that combining enzyme promiscuity and photo-/electro-redox catalysis can unlock new asymmetric reactions. This minireview highlights these emerging strategies and covers the literature from 2016 to date. Furthermore, the future development direction of this field is prospected.

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Electrochemically Tuned Oxidative [4+2] Annulation and Dioxygenation of Olefins with Hydroxamic Acids

et al. 2020

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This work represents the first [4+2] annulation of hydroxamic acids with olefins for the synthesis of benzo[c][1,2]oxazines scaffold via anode‐selective electrochemical oxidation. This protocol features mild conditions, is oxidant free, shows high regioselectivity and stereoselectivity, broad substrate scope of both alkenes and hydroxamic acids, and is compatible with terpenes, peptides, and steroids. Significantly, the dioxygenation of olefins employing hydroxamic acid is also successfully achieved by switching the anode material under the same reaction conditions. The study not only reveals a new reactivity of hydroxamic acids and its first application in electrosynthesis but also provides a successful example of anode material‐tuned product selectivity.

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Cu^II/TEMPO‐Catalyzed Enantioselective C(sp³)–H Alkynylation of Tertiary Cyclic Amines through Shono‐Type Oxidation

Cited by 28 publications

References 92 publications

Transition Metal‐Catalyzed C−H Functionalization Through Electrocatalysis

Transition Metal‐Catalyzed C−H Functionalization Through Electrocatalysis

Emerging Strategies for Asymmetric Synthesis: Combining Enzyme Promiscuity and Photo‐/Electro‐redox Catalysis

Electrochemically Tuned Oxidative [4+2] Annulation and Dioxygenation of Olefins with Hydroxamic Acids

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CuII/TEMPO‐Catalyzed Enantioselective C(sp3)–H Alkynylation of Tertiary Cyclic Amines through Shono‐Type Oxidation

Cited by 28 publications

References 92 publications

Transition Metal‐Catalyzed C−H Functionalization Through Electrocatalysis

Transition Metal‐Catalyzed C−H Functionalization Through Electrocatalysis

Emerging Strategies for Asymmetric Synthesis: Combining Enzyme Promiscuity and Photo‐/Electro‐redox Catalysis

Electrochemically Tuned Oxidative [4+2] Annulation and Dioxygenation of Olefins with Hydroxamic Acids

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Cu^II/TEMPO‐Catalyzed Enantioselective C(sp³)–H Alkynylation of Tertiary Cyclic Amines through Shono‐Type Oxidation