Photocatalyzed Coupling–Cyclization of <i>ortho</i>-Alkynylaryl Vinylethers with Arylsulfonyl Azides

Chen, Fengjuan; Huang, Xiang; Yang, Can; Jiang, Huanfeng; Zeng, Wei

doi:10.1021/acs.joc.1c01437

Cited by 9 publications

(1 citation statement)

References 72 publications

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“…Thereafter, the same group further expanded their strategy for the synthesis of carbosulfonylated 97 and [2 + 2 + 3] cyclized product 98 via fac-Ir(ppy) 3 photocatalyzed cyclization of 1,6enynes 61 with arylsulfonyl azides 91 (Scheme 30). [73] The authors found out that in the presence of THF, the reaction resulted in the formation of carbosulfonylated product 97, in which the THF is utilized as an H-atom source. On the other hand, when the reaction was performed in MeCN, a The applications of photo-induced atom transfer radical cyclization (ATRC) reactions has gained interest among chemist as it allows the addition of C-heteroatom and heteroatomheteroatom bonds across multiple bonds.…”

Section: Chemcatchemmentioning

confidence: 99%

Visible Light‐Mediated Manipulation of 1,n‐Enynes in Organic Synthesis

2022

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The 1,n-enynes are potent scaffolds in organic synthesis, providing a state-of-the-art approach for synthesizing various acyclic and carbo-and heterocyclic compounds. Radical cascade cyclization and CÀ H functionalization of 1,n-enynes have gained immense attention in the synthetic community. Significant advancement in this field has been developed over the years, employing harsh and expensive metal catalysts usually associated with intense product purification and unwanted side-products. In this context, the advent of visible light photocatalysis as a mild and efficient approach in the area of 1,nenynes is a welcome step. Herein, we provide an exclusive overview of the recent developments in visible light-assisted manipulation of 1,n-enynes. We have classified the review into 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, and 1,8-enynes, as well as dienyne, and enediyne-based reactions.

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Section: Chemcatchemmentioning

confidence: 99%

Visible Light‐Mediated Manipulation of 1,n‐Enynes in Organic Synthesis

2022

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Sulfonyl Nitrene and Amidyl Radical: Structure and Reactivity

Zelenka

Pereverzev

Jahn

et al. 2022

Chemistry A European J

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Photocatalytic generation of nitrenes and radicals can be used to tune or even control their reactivity. Photocatalytic activation of sulfonyl azides leads to the elimination of N2 and the resulting reactive species initiate C−H activations and amide formation reactions. Here, we present reactive radicals that are generated from sulfonyl azides: sulfonyl nitrene radical anion, sulfonyl nitrene and sulfonyl amidyl radical, and test their gas phase reactivity in C−H activation reactions. The sulfonyl nitrene radical anion is the least reactive and its reactivity is governed by the proton coupled electron transfer mechanism. In contrast, sulfonyl nitrene and sulfonyl amidyl radicals react via hydrogen atom transfer pathways. These reactivities and detailed characterization of the radicals with vibrational spectroscopy and with DFT calculations provide information necessary for taking control over the reactivity of these intermediates.

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Visible-light-mediated synthesis of functionalized benzofurans: an update

Kushwaha

2024

Chem Heterocycl Comp

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Photocatalyzed Coupling–Cyclization of ortho-Alkynylaryl Vinylethers with Arylsulfonyl Azides

Cited by 9 publications

References 72 publications

Visible Light‐Mediated Manipulation of 1,n‐Enynes in Organic Synthesis

Visible Light‐Mediated Manipulation of 1,n‐Enynes in Organic Synthesis

Sulfonyl Nitrene and Amidyl Radical: Structure and Reactivity

Visible-light-mediated synthesis of functionalized benzofurans: an update

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