N-Arylation of primary and tertiary sulfonimidamides (SIAs) with benzyne precursors under transition metal-free conditions

Ambala, Srinivas; Govender, Kimberleigh B.; Rajbongshi, Kamal Krishna; Govender, Thavendran; Kruger, Hendrik G.; Naicker, Tricia; Arvidsson, Per I.

doi:10.1016/j.tetlet.2023.154583

Tetrahedron Letters

2023

DOI: 10.1016/j.tetlet.2023.154583

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N-Arylation of primary and tertiary sulfonimidamides (SIAs) with benzyne precursors under transition metal-free conditions

Srinivas Ambala

Kimberleigh B. Govender

Kamal Krishna Rajbongshi

et al.

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2024

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Aryne Chemistry: Generation Methods and Reactions Incorporating Multiple Arynes

Kim,

Choi,

Suh

et al. 2024

Chem. Rev.

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Arynes hold significance for the efficient fusion of (hetero) arenes with diverse substrates, advancing the construction of complex molecular frameworks. Employing multiple equivalents of arynes is particularly effective in the rapid formation of polycyclic cores found in optoelectronic materials and bioactive compounds. However, the inherent reactivity of arynes often leads to side reactions, yielding unanticipated products and underlining the importance of a detailed investigation into the use of multiple arynes to fine-tune their reactivity. This review centers on methodologies and syntheses in organic reactions involving multiple arynes, categorizing based on mechanisms like cycloadditions, σ-bond insertions, nucleophilic additions, and ene reactions, and discusses aryne polymerization. The categorization based on these mechanisms includes two primary approaches: the first entails multiple aryne engagement within a single step while the second approach involves using a single equivalent of aryne sequentially across multiple steps, with both requiring strict reactivity control to ensure precise aryne participation in each respective step. Additionally, the review provides an in-depth analysis of the selection of aryne precursors, organized chronologically and by activation strategy, offering a comprehensive background that supports the main theme of multiple aryne utilization. The expectation remains that this comprehensive review will be invaluable in designing advanced syntheses engaging multiple arynes.

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Aryne Chemistry: Generation Methods and Reactions Incorporating Multiple Arynes

Kim,

Choi,

Suh

et al. 2024

Chem. Rev.

View full text Add to dashboard Cite

show abstract

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N-Arylation of primary and tertiary sulfonimidamides (SIAs) with benzyne precursors under transition metal-free conditions

Cited by 1 publication

References 38 publications

Aryne Chemistry: Generation Methods and Reactions Incorporating Multiple Arynes

Aryne Chemistry: Generation Methods and Reactions Incorporating Multiple Arynes

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