Revealing the nature of covalently tethered distonic radical anions in the generation of heteroatom-centered radicals: evidence for the polarity-matching PCET pathway

Fu, Kang; Yang, Xihui; Yu, Zhiyou; Song, Lijuan; Shi, Lei

doi:10.1039/d4sc02602k

Chem. Sci.

2024

DOI: 10.1039/d4sc02602k

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Revealing the nature of covalently tethered distonic radical anions in the generation of heteroatom-centered radicals: evidence for the polarity-matching PCET pathway

Kang Fu,

Xihui Yang,

Zhiyou Yu

et al.

Abstract: Recognition on the intermediacy and regulation on reactivity patterns of radical intermediates in radical chemistry make profound impacts on harnessing and developing the full potential of open-shell species in synthetic...

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Cited by 3 publications

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Manganese‐Mediated Cascade Radical Oxidative Cyclization/1,6‐Conjugate Addition of Unsaturated Oximes with p‐Quinone Methides: Facile Access to β,β‐Diarylmethine Substituted Isoxazolines

Vara,

Thete,

Ghotekar

et al. 2024

Chemistry An Asian Journal

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A simple and efficient strategy for the synthesis of structurally diverse β,β‐diarylmethine substituted isoxazoline derivatives have been developed. This approach employs a manganese‐promoted oxidative cyclization coupled with a 1,6‐conjugate addition of unsaturated oximes to p‐quinone methides. The key features of this study include the formation of C‐O and C‐C bonds through intramolecular and intermolecular interactions, facilitated by in situ generated iminoxyl radicals. β,β‐diarylmethine substituted isoxazolines, bearing a wide range of functional groups, were isolated in high yields

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Manganese‐Mediated Cascade Radical Oxidative Cyclization/1,6‐Conjugate Addition of Unsaturated Oximes with p‐Quinone Methides: Facile Access to β,β‐Diarylmethine Substituted Isoxazolines

Vara,

Thete,

Ghotekar

et al. 2024

Chemistry An Asian Journal

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Enabling Site-Selective C–H Functionalization of Aliphatic Alcohols and Amines with exo-Directing Groups by Tether-Tunable Design of Pd^II/Pd^IV Catalysis

Fu,

Shi

2024

ACS Catal.

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We report herein a general platform for palladium catalysis using a library of cyclic diacyl peroxides, achieving siteselective C−H functionalization of aliphatic alcohols and amines. Experimental studies and theoretical calculations indicate that bystanding cyclic diacyl peroxides minimize unwanted reductive elimination events and enable controlled C−H cleavage. The protocol is simple and scalable and offers high selectivity and a broad range of substrates and nucleophiles, including complex molecules. The findings advance understanding of high-valent palladium chemistry, providing a tool for creating chemically diverse vicinal diols and amino alcohols and opening new possibilities in C−H functionalization.

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Photoinduced cross-coupling of aryl halides enabled by n-tetrabutylphosphonium phthalate

Tian,

Shi

2024

Org. Chem. Front.

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Revealing the nature of covalently tethered distonic radical anions in the generation of heteroatom-centered radicals: evidence for the polarity-matching PCET pathway

Abstract: Recognition on the intermediacy and regulation on reactivity patterns of radical intermediates in radical chemistry make profound impacts on harnessing and developing the full potential of open-shell species in synthetic...

Cited by 3 publications

References 64 publications

Manganese‐Mediated Cascade Radical Oxidative Cyclization/1,6‐Conjugate Addition of Unsaturated Oximes with p‐Quinone Methides: Facile Access to β,β‐Diarylmethine Substituted Isoxazolines

Manganese‐Mediated Cascade Radical Oxidative Cyclization/1,6‐Conjugate Addition of Unsaturated Oximes with p‐Quinone Methides: Facile Access to β,β‐Diarylmethine Substituted Isoxazolines

Enabling Site-Selective C–H Functionalization of Aliphatic Alcohols and Amines with exo-Directing Groups by Tether-Tunable Design of Pd^II/Pd^IV Catalysis

Photoinduced cross-coupling of aryl halides enabled by n-tetrabutylphosphonium phthalate

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Revealing the nature of covalently tethered distonic radical anions in the generation of heteroatom-centered radicals: evidence for the polarity-matching PCET pathway

Abstract: Recognition on the intermediacy and regulation on reactivity patterns of radical intermediates in radical chemistry make profound impacts on harnessing and developing the full potential of open-shell species in synthetic...

Cited by 3 publications

References 64 publications

Manganese‐Mediated Cascade Radical Oxidative Cyclization/1,6‐Conjugate Addition of Unsaturated Oximes with p‐Quinone Methides: Facile Access to β,β‐Diarylmethine Substituted Isoxazolines

Manganese‐Mediated Cascade Radical Oxidative Cyclization/1,6‐Conjugate Addition of Unsaturated Oximes with p‐Quinone Methides: Facile Access to β,β‐Diarylmethine Substituted Isoxazolines

Enabling Site-Selective C–H Functionalization of Aliphatic Alcohols and Amines with exo-Directing Groups by Tether-Tunable Design of PdII/PdIV Catalysis

Photoinduced cross-coupling of aryl halides enabled by n-tetrabutylphosphonium phthalate

Contact Info

Product

Resources

About

Enabling Site-Selective C–H Functionalization of Aliphatic Alcohols and Amines with exo-Directing Groups by Tether-Tunable Design of Pd^II/Pd^IV Catalysis