Palladium(<scp>ii</scp>)-catalyzed intramolecular C–H amination to carbazole: the crucial role of cyclic diacyl peroxides

Yuan, Ting; Fu, Kang; Shi, Lei

doi:10.1039/d4qo00779d

Org. Chem. Front.

2024

DOI: 10.1039/d4qo00779d

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Palladium(ii)-catalyzed intramolecular C–H amination to carbazole: the crucial role of cyclic diacyl peroxides

Ting Yuan,

Kang Fu,

Lei Shi

Abstract: Herein, we have developed an efficient PdII-catalyzed intramolecular oxidative C–H amination under additive-free and green conditions where strained cyclic diacyl peroxide functions as both a sacrificial oxidant and a bidentate linker.

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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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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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Palladium(ii)-catalyzed intramolecular C–H amination to carbazole: the crucial role of cyclic diacyl peroxides

Abstract: Herein, we have developed an efficient PdII-catalyzed intramolecular oxidative C–H amination under additive-free and green conditions where strained cyclic diacyl peroxide functions as both a sacrificial oxidant and a bidentate linker.

Cited by 1 publication

References 82 publications

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

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

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Palladium(ii)-catalyzed intramolecular C–H amination to carbazole: the crucial role of cyclic diacyl peroxides

Abstract: Herein, we have developed an efficient PdII-catalyzed intramolecular oxidative C–H amination under additive-free and green conditions where strained cyclic diacyl peroxide functions as both a sacrificial oxidant and a bidentate linker.

Cited by 1 publication

References 82 publications

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

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

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

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