Visible-Light-Driven Synthesis of 4-Alkyl/Aryl-2-Aminothiazoles Promoted by In Situ Generated Copper Photocatalyst

Lei, Wen-Long; Wang, Tao; Feng, Kaiwen; Wu, Li‐Zhu; Liu, Qiang

doi:10.1021/acscatal.7b02818

Cited by 75 publications

(32 citation statements)

References 61 publications

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“…It has been applied to the synthesis of natural products, including γ‐asarone. The methods reported separately by Liu et al [32] . and Patil et al [33] .…”

Section: Resultsmentioning

confidence: 99%

“…It has been applied to the synthesis of natural products, including γ-asarone. The methods reported separately by Liu et al [32] and Patil et al [33] can be carried out at room temperature in the presence of metal catalyst. Our method shown in Scheme 5 required 50°C for the Claisen-type rearrangement to take place.…”

Section: Comparison Of the Three Reactions In Scheme 1 With The Estabmentioning

confidence: 99%

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Domino Processes of Arynes Reacting with Three Classes of Nucleophiles for Organic Syntheses

et al. 2021

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Synthetic application of arynes is broadened by their reactions with neutral N-, Sand nd O-containing nucleophiles to produce three types of compounds. Accordingly, 1,2-dihydroquinolines are synthesized from Schiff bases, alkynes, and arynes through a Diels-Alder reaction. Epoxides are prepared from thioethers and arynes along with aldehydes or ketones through a Johnson-Corey-Chaykovsky reaction. Phenolic ethers are produced from allyl ethers and arynes through a Claisen-type rearrangement. These target molecules, including natural products γ-asarone, asaricin, and a cholesteryl phenolic ether, are formed through reactions initiated by arynes. These new reactions share a prevailing feature of domino processes, which are carried out in a single flask and afford the desired products in good to high yields.

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“…It has been applied to the synthesis of natural products, including γ‐asarone. The methods reported separately by Liu et al [32] . and Patil et al [33] .…”

Section: Resultsmentioning

confidence: 99%

Section: Comparison Of the Three Reactions In Scheme 1 With The Estabmentioning

confidence: 99%

Domino Processes of Arynes Reacting with Three Classes of Nucleophiles for Organic Syntheses

et al. 2021

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“…49 In addition, Liu group has disclosed a new methodology about synthesizing a broad range of 4-alkyl/aryl-2-aminothiazoles via copper-promoted intermolecular cyclization of vinyl azides under visible-light irradiation (Scheme 29). 50 In the catalytic cycle (figure 13), the in situ formed copper catalyst plays dual roles in the transformation: (1) as the photocatalyst to activate vinyl azides, (2) as the Lewis acid catalyst to promote ring opening of 2H-azirines with thiocyanide.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

Recent Advances in Visible-Light-Promoted Copper Catalysis in Organic Reactions

Xiong

Xiao

et al. 2021

Synthesis

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In recent years, visible-light-mediated copper photocatalysis have emerged as an attractive strategy for the diverse constructions of basic bonds in an ecologically benign and cost-effective fashion. The intense activity and increasing work of these areas stimulated the exploit of the distinctive properties of copper photocatalysis and the rapid development and expansion of their applications. In this review, we focus on introducing a series of significant achievements in copper complexes as standalone photocatalysis in organic reactions to make an attempt to exhibit their potential capabilities and high flexibilities in synthetic chemistry.

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“…In 2017, Wu, Liu, and co-workers accomplished a visible-light-induced, copper salt catalyzed construction of thiazoles 182 without a photocatalyst (Scheme 78). 54 In this process, the generated Cu(NCS) 2 plays a dual role as both photosensitizer and Lewis acid. Under the optimized conditions, various vinyl azides with different functional groups were all well tolerated.…”

Section: Scheme 77 Proposed Mechanism For the Photoinduced Copper-catmentioning

confidence: 99%

Visible-Light-Driven Organic Photochemical Reactions in the Absence of External Photocatalysts

et al. 2019

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Visible-light-driven organic photochemical reactions have attracted substantial attention from the synthetic community. Typically, catalytic quantities of photosensitizers, such as transition metal complexes, organic dyes, or inorganic semiconductors, are necessary to absorb visible light and trigger subsequent organic transformations. Recently, in contrast to these photocatalytic processes, a variety of photocatalyst-free organic photochemical transformations have been exploited for the efficient formation of carbon–carbon and carbon–heteroatom bonds. In addition to not requiring additional photocatalysts, they employ low-energy visible light irradiation, have mild reaction conditions, and enable broad substrate diversity and functional group tolerance. This review will focus on a summary of representative work in this field in terms of different photoexcitation modes.1 Introduction2 Visible Light Photoexcitation of a Single Substrate3 Visible Light Photoexcitation of Reaction Intermediates4 Visible Light Photoexcitation of EDA Complexes between Substrates5 Visible Light Photoexcitation of EDA Complexes between Substrates and Reaction Intermediates6 Visible Light Photoexcitation of Products7 Conclusion and Outlook

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Visible-Light-Driven Synthesis of 4-Alkyl/Aryl-2-Aminothiazoles Promoted by In Situ Generated Copper Photocatalyst

Cited by 75 publications

References 61 publications

Domino Processes of Arynes Reacting with Three Classes of Nucleophiles for Organic Syntheses

Domino Processes of Arynes Reacting with Three Classes of Nucleophiles for Organic Syntheses

Recent Advances in Visible-Light-Promoted Copper Catalysis in Organic Reactions

Visible-Light-Driven Organic Photochemical Reactions in the Absence of External Photocatalysts

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