Radical-mediated [3 + 2 + 1] annulation of α-polyfluoromethyl alkenes with arylisocyanates enabled by C(sp<sup>3</sup>)–F activation

Yang, Yu-Zhong; Xue, Qi; Sun, Qing; Li, Yang; Hu, Ming; Xu, Chong-Hui; Li, Jin-Heng

doi:10.1039/d3qo02054a

Org. Chem. Front.

2024

DOI: 10.1039/d3qo02054a

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Radical-mediated [3 + 2 + 1] annulation of α-polyfluoromethyl alkenes with arylisocyanates enabled by C(sp³)–F activation

Yu-Zhong Yang,

Qi Xue,

Qing Sun

et al.

Abstract: Direct C(sp3)-F functionalization represents an attractively powerful technology for further modification to construct diverse value-added fluorinated structures and enable environmentally persistent fluorinated molecule degradation. However, direct C(sp3)-F activation of alkenyl-CF3...

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Cited by 3 publications

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One‐Pot Reactions of Ynones with Isothiocyanates for Accessing 2‐Aminothiophenone and Indole‐Fused/Indole‐Substituted Thiophenone Derivatives

Jin,

Li,

Shen

et al. 2024

Adv Synth Catal

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A copper or silver‐catalyzed cascade addition/5‐exo‐dig cyclization/isomerization reaction of isothiocyanate with ynone has been developed. This strategy enables the synthesis of a variety of (Z)‐2‐ylidene‐5‐aminothiophen‐3‐one derivatives with diverse substitutions in a single vessel. The method is featured with pot‐economy and high regio‐ and Z‐selectivity. Several biologically active molecules could be modified using this strategy. Moreover, the relevant indole‐fused and indole‐substituted thiophenone derivatives were also assembled in one pot by merging this strategy with other bond formation methods. Based on the experiments and the related reports, a cascade pathway triggered by the addition of ynone‐derived radical towards the C(sp)‐atom of isothiocyanate was proposed to elucidate the probable process of the transformation.

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One‐Pot Reactions of Ynones with Isothiocyanates for Accessing 2‐Aminothiophenone and Indole‐Fused/Indole‐Substituted Thiophenone Derivatives

Jin,

Li,

Shen

et al. 2024

Adv Synth Catal

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Efficient and regioselective C=S bond difunctionalization through a three-component radical relay strategy

Li,

Luo,

Liang

et al. 2024

Chinese Chemical Letters

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Multi-functionalization of β-trifluoromethyl enones enabled 2,3-dihydrofuran synthesis

Hu,

Han,

Chen

et al. 2024

Org. Chem. Front.

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Radical-mediated [3 + 2 + 1] annulation of α-polyfluoromethyl alkenes with arylisocyanates enabled by C(sp³)–F activation

Abstract: Direct C(sp3)-F functionalization represents an attractively powerful technology for further modification to construct diverse value-added fluorinated structures and enable environmentally persistent fluorinated molecule degradation. However, direct C(sp3)-F activation of alkenyl-CF3...

Cited by 3 publications

References 82 publications

One‐Pot Reactions of Ynones with Isothiocyanates for Accessing 2‐Aminothiophenone and Indole‐Fused/Indole‐Substituted Thiophenone Derivatives

One‐Pot Reactions of Ynones with Isothiocyanates for Accessing 2‐Aminothiophenone and Indole‐Fused/Indole‐Substituted Thiophenone Derivatives

Efficient and regioselective C=S bond difunctionalization through a three-component radical relay strategy

Multi-functionalization of β-trifluoromethyl enones enabled 2,3-dihydrofuran synthesis

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Radical-mediated [3 + 2 + 1] annulation of α-polyfluoromethyl alkenes with arylisocyanates enabled by C(sp3)–F activation

Abstract: Direct C(sp3)-F functionalization represents an attractively powerful technology for further modification to construct diverse value-added fluorinated structures and enable environmentally persistent fluorinated molecule degradation. However, direct C(sp3)-F activation of alkenyl-CF3...

Cited by 3 publications

References 82 publications

One‐Pot Reactions of Ynones with Isothiocyanates for Accessing 2‐Aminothiophenone and Indole‐Fused/Indole‐Substituted Thiophenone Derivatives

One‐Pot Reactions of Ynones with Isothiocyanates for Accessing 2‐Aminothiophenone and Indole‐Fused/Indole‐Substituted Thiophenone Derivatives

Efficient and regioselective C=S bond difunctionalization through a three-component radical relay strategy

Multi-functionalization of β-trifluoromethyl enones enabled 2,3-dihydrofuran synthesis

Contact Info

Product

Resources

About

Radical-mediated [3 + 2 + 1] annulation of α-polyfluoromethyl alkenes with arylisocyanates enabled by C(sp³)–F activation