Catalyst-free tandem reaction of 2,2′-diaminodiphenyldisulfides, sulfinic acids and aromatic aldehydes: an approach to synthesize unsymmetric thiosulfonates and benzothiazoles

Zhou, Chao; Ye, Ruyi; Meng, Ling‐Guo

doi:10.1039/d1gc04878c

Green Chem.

2022

DOI: 10.1039/d1gc04878c

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Catalyst-free tandem reaction of 2,2′-diaminodiphenyldisulfides, sulfinic acids and aromatic aldehydes: an approach to synthesize unsymmetric thiosulfonates and benzothiazoles

Chao Zhou

Ruyi Ye

Ling‐Guo Meng

Abstract: A facile, efficient and green synthetic method for the preparation of unsymmetric S-(2-aminophenyl) arenethiosulfonates and 2-arylbenzothiazoles through a tandem reaction of 2,2′-diaminodiaryldisulfides, arylsulfinic acids and aromatic aldehydes was developed. Mechanistic...

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Cited by 5 publications

References 37 publications

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Interweavable Metalloporphyrin‐Based Fibers for Indirect Electrocatalysis

Yao,

Liu,

Huang

et al. 2024

Angewandte Chemie

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The applications of indirect electrocatalysis toward potential industrial processes are drastically limited by the utilization or processing forms of electrocatalysts. The remaining challenges of electrocatalysts like the recycling in homogeneous systems or pulverization in heterogeneous systems call for advanced processing forms to meet the desired requirements. Here, we report a series of metalloporphyrin‐based polymer fibers (M‐PF, M = Ni, Cu and Zn) through a rigid‐flexible polymerization strategy based on rigid metalloporphyrin and flexible thiourea units that can be applied as heterogenous redox‐mediators in indirect electrocatalysis. These functional fibers with high strength and flexibility exhibit interweavable and designable functions that can be processed into different fiber‐forms like knotted, two‐spiral, three‐ply, five‐ply fibers or even interweaved networks. Interestingly, they can be readily applied in S‐S bond cleaving/cyclization reaction or extended oxidative self‐coupling reaction of thiols with high efficiency. Remarkably, it enables the scale‐up production (1.25 g in a batch‐experiment) under laboratory conditions.

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Interweavable Metalloporphyrin‐Based Fibers for Indirect Electrocatalysis

Yao,

Liu,

Huang

et al. 2024

Angewandte Chemie

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Interweavable Metalloporphyrin‐Based Fibers for Indirect Electrocatalysis

Yao,

Liu,

Huang

et al. 2024

Angew Chem Int Ed

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Synthesis of Unsymmetric Thiosulfonates Starting from N-Substituted O-Thiocarbamates: Easy Access to the S–SO₂ Bond

et al. 2022

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Using phenyliodine diacetate as an oxidant and nickel acetate as a promoter, a wide range of unsymmetric thiosulfonates could be furnished easily in moderate to excellent yields starting from N-substituted O-thiocarbamates and sodium sulfinates. This protocol features mild conditions, short reaction times, and high atomic utilization, which can provide an alternative method for the synthesis of unsymmetric thiosulfonates. In addition, the reaction could be scaled up on a gram scale, showing potential application value in industry.

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Catalyst-free tandem reaction of 2,2′-diaminodiphenyldisulfides, sulfinic acids and aromatic aldehydes: an approach to synthesize unsymmetric thiosulfonates and benzothiazoles

Abstract: A facile, efficient and green synthetic method for the preparation of unsymmetric S-(2-aminophenyl) arenethiosulfonates and 2-arylbenzothiazoles through a tandem reaction of 2,2′-diaminodiaryldisulfides, arylsulfinic acids and aromatic aldehydes was developed. Mechanistic...

Cited by 5 publications

References 37 publications

Interweavable Metalloporphyrin‐Based Fibers for Indirect Electrocatalysis

Interweavable Metalloporphyrin‐Based Fibers for Indirect Electrocatalysis

Interweavable Metalloporphyrin‐Based Fibers for Indirect Electrocatalysis

Synthesis of Unsymmetric Thiosulfonates Starting from N-Substituted O-Thiocarbamates: Easy Access to the S–SO₂ Bond

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Catalyst-free tandem reaction of 2,2′-diaminodiphenyldisulfides, sulfinic acids and aromatic aldehydes: an approach to synthesize unsymmetric thiosulfonates and benzothiazoles

Abstract: A facile, efficient and green synthetic method for the preparation of unsymmetric S-(2-aminophenyl) arenethiosulfonates and 2-arylbenzothiazoles through a tandem reaction of 2,2′-diaminodiaryldisulfides, arylsulfinic acids and aromatic aldehydes was developed. Mechanistic...

Cited by 5 publications

References 37 publications

Interweavable Metalloporphyrin‐Based Fibers for Indirect Electrocatalysis

Interweavable Metalloporphyrin‐Based Fibers for Indirect Electrocatalysis

Interweavable Metalloporphyrin‐Based Fibers for Indirect Electrocatalysis

Synthesis of Unsymmetric Thiosulfonates Starting from N-Substituted O-Thiocarbamates: Easy Access to the S–SO2 Bond

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Product

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Synthesis of Unsymmetric Thiosulfonates Starting from N-Substituted O-Thiocarbamates: Easy Access to the S–SO₂ Bond