Deep eutectic solvents as sustainable media for multicomponent sulfonylation: an efficient strategy to synthesize (hetero)aryl sulfones

Zhu, Haibo; Zhong, Yangbo; Yan, Liyuan; Zhang, Honglei; Shen, Yajing; Le, Zhanggao; Fan, Qiangwen; Xie, Zongbo

doi:10.1039/d3gc04395a

Green Chem.

2024

DOI: 10.1039/d3gc04395a

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Deep eutectic solvents as sustainable media for multicomponent sulfonylation: an efficient strategy to synthesize (hetero)aryl sulfones

Haibo Zhu,

Yangbo Zhong,

Liyuan Yan

et al.

Abstract: Synthesis of valuable sulfone compounds directly from insertion of SO2 is an area of great interest in chemical research. However, the preparation of functional sulfones from transition-metal catalysis currently relies...

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Cited by 3 publications

References 63 publications

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Cross‐Coupling of Gaseous Alkanes with (Hetero)Aryl Bromides via Dual Nickel/Photoredox Catalysis

Nair,

Martínez‐Balart,

Barbeira‐Arán

et al. 2024

Angewandte Chemie

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Gaseous alkanes represent the most abundant carbon‐based chemical feedstocks in our planet. However, the intrinsic inertness of their C‐H bonds has rendered the use of these alkanes very difficult for purposes beyond aerobic combustion and energy intensive processes. Thus, clean and energy‐efficient transformations for their use in synthetic organic chemistry are still rare. Here we report a catalytic methodology for the direct cross‐coupling of gaseous alkanes with (hetero)aryl bromides through the combination of metallaphotoredox‐mediated hydrogen atom transfer and nickel catalysis. This protocol provides an efficient platform for the addition of short alkyl groups into diverse (hetero) aromatic rings, providing a wide range of high‐value alkyl(hetero)arenes, and bypassing the longstanding need of using preactivated alkylating agents in C(sp2)‐C(sp3) cross‐couplings. The method features high chemoselectivity, regioselectivity and a remarkable functional group tolerance, operates under mild conditions, and exhibits operational simplicity

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Cross‐Coupling of Gaseous Alkanes with (Hetero)Aryl Bromides via Dual Nickel/Photoredox Catalysis

Nair,

Martínez‐Balart,

Barbeira‐Arán

et al. 2024

Angewandte Chemie

View full text Add to dashboard Cite

show abstract

Cross‐Coupling of Gaseous Alkanes with (Hetero)Aryl Bromides via Dual Nickel/Photoredox Catalysis

Nair,

Martínez‐Balart,

Barbeira‐Arán

et al. 2024

Angew Chem Int Ed

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Electrochemical Sulfonylation/Cyclization of N-Alkenylacrylamides with Sodium Sulfinates or Sulfonyl Hydrazides

Yang,

Ding,

Yang

et al. 2024

J. Org. Chem.

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Two general protocols for the regioselective electrochemically enabled sulfonylation cyclization of Nalkenylacrylamides with sodium sulfinates or sulfonyl hydrazides were described. These methods were carried out under mild, chemical oxidant-free, and transition-metal-free conditions with a broad substrate scope and good functional group tolerance to provide sulfonyl-containing 4-pyrrolin-2-ones, which is readily scalable to the gram scale.

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Deep eutectic solvents as sustainable media for multicomponent sulfonylation: an efficient strategy to synthesize (hetero)aryl sulfones

Abstract: Synthesis of valuable sulfone compounds directly from insertion of SO2 is an area of great interest in chemical research. However, the preparation of functional sulfones from transition-metal catalysis currently relies...

Cited by 3 publications

References 63 publications

Cross‐Coupling of Gaseous Alkanes with (Hetero)Aryl Bromides via Dual Nickel/Photoredox Catalysis

Cross‐Coupling of Gaseous Alkanes with (Hetero)Aryl Bromides via Dual Nickel/Photoredox Catalysis

Cross‐Coupling of Gaseous Alkanes with (Hetero)Aryl Bromides via Dual Nickel/Photoredox Catalysis

Electrochemical Sulfonylation/Cyclization of N-Alkenylacrylamides with Sodium Sulfinates or Sulfonyl Hydrazides

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