Sulfoximines Assisted Rh(III)-Catalyzed C–H Activation/Annulation Cascade to Synthesize Highly Fused Indeno-1,2-benzothiazines

Li, Jian; Li, Hui; Fang, Daqing; Liu, Lingjun; Han, Xu; Sun, Jina; Li, Chunpu; Zhou, Yu; Ye, Deju; Liu, Hong

doi:10.1021/acs.joc.1c01820

Cited by 16 publications

(5 citation statements)

References 63 publications

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“…1 4). 15 A reaction tube was charged with a mixture of 3aa (55.3 mg, 0.2 mmol), and LiCl (8.5 mg, 0.2 mmol, 1.0 equiv) in THF (5 mL). To the mixture was added NaBH 4 (45.4 mg, 1.2 mmol, 6.0 equiv) in small portions in an ice bath, and subsequently methanol (1 mL) was added dropwise.…”

Section: N-(7-methoxy-10-oxoindeno[12-b]indol-5(10h)-yl)acetamide (3ra)mentioning

confidence: 99%

Rhodium(III)-Catalyzed C–H Cascade Annulation of Arylhydrazines with 2-Diazo-1,3-indandiones for the Synthesis of Tetracyclic Indeno[1,2-b]indoles

Li,

Lu,

et al. 2024

J. Org. Chem.

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An efficient approach for the preparation of tetracyclic indeno [1,2-b]indoles via Rh(III)-catalyzed C−H cascade annulation between arylhydrazines and diazo indan-1,3diones has been established. In addition, a series of indeno[1,2b]indoles were obtained in up to 96% yield with a wide range of substrates and high functional group tolerance. Finally, the diverse transformations of the desired products demonstrate the synthetic utility and utilization of this protocol.

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Section: N-(7-methoxy-10-oxoindeno[12-b]indol-5(10h)-yl)acetamide (3ra)mentioning

confidence: 99%

Rhodium(III)-Catalyzed C–H Cascade Annulation of Arylhydrazines with 2-Diazo-1,3-indandiones for the Synthesis of Tetracyclic Indeno[1,2-b]indoles

Li,

Lu,

et al. 2024

J. Org. Chem.

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“…Directing groups, which act through direct interaction of the sulfur atom with the metal, should be distinguished from N‐ or O‐coordinating groups containing sulfur, such as sulfoximines [44–46] and sulfoxides [47–49] . This review considers only S‐coordinating C−H‐activation directing groups that are synthetically important in C−C bond formation reactions [50–67] .…”

Section: C−h Activationmentioning

confidence: 99%

Sulfur in Waste‐Free Sustainable Synthesis: Advancing Carbon–Carbon Coupling Techniques

Shlapakov,

Kobelev,

Burykina

et al. 2024

Angew Chem Int Ed

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This review explores the pivotal role of sulfur in advancing sustainable carbon‐carbon (C–C) coupling reactions. The unique electronic properties of sulfur, as a soft Lewis base with significant mesomeric effect make it an excellent candidate for initiating radical transformations, directing C–H‐activation, and facilitating cycloaddition and C–S bond dissociation reactions. These attributes are crucial for developing waste‐free methodologies in green chemistry. Our mini‐review is focused on existing sulfur‐directed C–C coupling techniques, emphasizing their sustainability and comparing state‐of‐the‐art methods with traditional approaches. The review highlights the importance of this research in addressing current challenges in organic synthesis and catalysis. The innovative use of sulfur in photocatalytic, electrochemical and metal‐catalyzed processes not only exemplifies significant advancements in the field but also opens new avenues for environmentally friendly chemical processes. By focusing on atom economy and waste minimization, the analysis provides broad appeal and potential for future developments in sustainable organic chemistry.

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“…In 2021, Ye and Liu and coworkers described a methodology for the synthesis of highly conjugated 1,2-benzothiazine scaffolds 25 using sulfoximines 23 and 2-diazo-1H-indene-1,3(2H)-diones 24 ( Scheme 12 ) [ 34 ]. The silver additive was proved to be important for high yields.…”

Section: Synthesis Of Cyclic Sulfoximines Via Intermolecular C–h Acti...mentioning

confidence: 99%

Recent Advances in the Synthesis of Cyclic Sulfoximines via C–H Bond Activation

2023

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Sulfoximines, a ubiquitous class of structural motifs, are widely present in bioactive molecules and functional materials that have received considerable attention from modern organic chemistry, pharmaceutical industries, and materials science. Sulfoximines have proved to be an effective directing group for C–H functionalization which was widely investigated for the synthesis of cyclic sulfoximines. Within the last decade, great progress has been achieved in the synthesis of cyclic sulfoximines. Thus, this review highlights the recent advances in the synthesis of cyclic sulfoximines via the C–H activation strategy and is classified based on the substrate types.

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Sulfoximines Assisted Rh(III)-Catalyzed C–H Activation/Annulation Cascade to Synthesize Highly Fused Indeno-1,2-benzothiazines

Cited by 16 publications

References 63 publications

Rhodium(III)-Catalyzed C–H Cascade Annulation of Arylhydrazines with 2-Diazo-1,3-indandiones for the Synthesis of Tetracyclic Indeno[1,2-b]indoles

Rhodium(III)-Catalyzed C–H Cascade Annulation of Arylhydrazines with 2-Diazo-1,3-indandiones for the Synthesis of Tetracyclic Indeno[1,2-b]indoles

Sulfur in Waste‐Free Sustainable Synthesis: Advancing Carbon–Carbon Coupling Techniques

Recent Advances in the Synthesis of Cyclic Sulfoximines via C–H Bond Activation

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