Mechanistic Insights into Tf<sub>2</sub>O-Promoted Electrophilic Activation of 2-Propynamides and a New Synthesis of 2,4-Disubstituted Quinolines

Shan, Lidong; Li, Hongchen; Zheng, Weiping; Wang, Xingyong; Wang, Xinyan

doi:10.1021/acs.orglett.2c03565

Org. Lett.

2022

DOI: 10.1021/acs.orglett.2c03565

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Mechanistic Insights into Tf₂O-Promoted Electrophilic Activation of 2-Propynamides and a New Synthesis of 2,4-Disubstituted Quinolines

Lidong Shan

Hongchen Li

Weiping Zheng

et al.

Abstract: Direct evidence explaining why 2-propynamides have never been used as substrates in Tf2O-promoted electrophilic activations was obtained. Furthermore, a new method for the synthesis of structurally special 2,4-disubstituted quinolines was developed, by which the substituent at position 2 of quinolines can be diversified easily.

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Cited by 2 publications

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FeCl₃-Catalyzed Decyanative [4 + 2] Annulation of α-Aminonitriles with Alkynes: Access to 2,4-Diaryl Quinolines in Batch and Continuous-Flow Processes

Sathyendran,

Muthu,

Govindan

et al. 2023

Org. Lett.

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FeCl3-catalyzed decyanation of α-aminonitriles followed by a [4 + 2] annulation with terminal alkynes has been developed to synthesize 2,4-diaryl quinolines. A broad range of aniline, aldehyde, and arylacetylene derivatives were well tolerated to access 2,4-diaryl quinolines in moderate to good yields. The control experiment studies suggested that the reaction proceeds through a nonradical pathway involving Povarov-type [4 + 2] annulation from the in situ generated iminium species. The synthetic application of this strategy (i) includes gram-scale synthesis and (ii) a continuous-flow process for a few representative compounds in a shorter reaction time (22 min) and (iii) worked well with styrene as a proof of concept.

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FeCl₃-Catalyzed Decyanative [4 + 2] Annulation of α-Aminonitriles with Alkynes: Access to 2,4-Diaryl Quinolines in Batch and Continuous-Flow Processes

Sathyendran,

Muthu,

Govindan

et al. 2023

Org. Lett.

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Chemospecific C3- and C2-Olefinations of Isatins by TfOH-Promoted Tandem Aldol-Grob and Semiacetalization-Grob Fragmentations

Shan

Liu

et al. 2023

Org. Lett.

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Mechanistic Insights into Tf₂O-Promoted Electrophilic Activation of 2-Propynamides and a New Synthesis of 2,4-Disubstituted Quinolines

Cited by 2 publications

References 44 publications

FeCl₃-Catalyzed Decyanative [4 + 2] Annulation of α-Aminonitriles with Alkynes: Access to 2,4-Diaryl Quinolines in Batch and Continuous-Flow Processes

FeCl₃-Catalyzed Decyanative [4 + 2] Annulation of α-Aminonitriles with Alkynes: Access to 2,4-Diaryl Quinolines in Batch and Continuous-Flow Processes

Chemospecific C3- and C2-Olefinations of Isatins by TfOH-Promoted Tandem Aldol-Grob and Semiacetalization-Grob Fragmentations

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Mechanistic Insights into Tf2O-Promoted Electrophilic Activation of 2-Propynamides and a New Synthesis of 2,4-Disubstituted Quinolines

Cited by 2 publications

References 44 publications

FeCl3-Catalyzed Decyanative [4 + 2] Annulation of α-Aminonitriles with Alkynes: Access to 2,4-Diaryl Quinolines in Batch and Continuous-Flow Processes

FeCl3-Catalyzed Decyanative [4 + 2] Annulation of α-Aminonitriles with Alkynes: Access to 2,4-Diaryl Quinolines in Batch and Continuous-Flow Processes

Chemospecific C3- and C2-Olefinations of Isatins by TfOH-Promoted Tandem Aldol-Grob and Semiacetalization-Grob Fragmentations

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Product

Resources

About

Mechanistic Insights into Tf₂O-Promoted Electrophilic Activation of 2-Propynamides and a New Synthesis of 2,4-Disubstituted Quinolines

FeCl₃-Catalyzed Decyanative [4 + 2] Annulation of α-Aminonitriles with Alkynes: Access to 2,4-Diaryl Quinolines in Batch and Continuous-Flow Processes

FeCl₃-Catalyzed Decyanative [4 + 2] Annulation of α-Aminonitriles with Alkynes: Access to 2,4-Diaryl Quinolines in Batch and Continuous-Flow Processes