Nickel-Catalyzed Selective C–H Cyanation via Aromatic Thianthrenium Salts

Zhang, Guofu; Luo, Zijin; Guan, Chenfei; Zhang, Xianghao; Ding, Chengrong

doi:10.1021/acs.joc.3c00814

Cited by 9 publications

(2 citation statements)

References 58 publications

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“…Firstly, the catalyst of NiCl 2 was reduced by Zn could initially undergo a radical process with thianthrenium salts, followed by transmetallation with Zn(CN) 2 and reductive elimination to complete the catalytic cycle (Scheme 4). [12]…”

Section: C(sp 2 )à C(sp) Bond Formationmentioning

confidence: 99%

Synthetic Applications of Sulfonium Salts as Aryl Radical Precursors

Wu,

Gao,

Chen

2023

Eur J Org Chem

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The utilization of aryl radicals as open‐shelled intermediates has become an essential tool for both conventional and state‐of‐the‐art synthetic chemistry. However, the current methods for generating aryl radicals are still inefficient, greatly impeding their practical applications. Encouragingly, sulfonium salts have emerged as appealing sources of aryl radicals for a wide range of transformations aimed at creating novel chemical bonds driven by their distinctive structural attributes and chemical tendencies. This review primarily focuses on the specific reaction mechanisms underlying the cleavage of C−S bonds in sulfonium salts, leading to the generation of corresponding aryl radicals within diverse reaction conditions.

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Section: C(sp 2 )à C(sp) Bond Formationmentioning

confidence: 99%

Synthetic Applications of Sulfonium Salts as Aryl Radical Precursors

Wu,

Gao,

Chen

2023

Eur J Org Chem

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“…Notably, they have successfully enabled the selective functionalization of inert chemical bonds, such as C–H, C–C, C–O, and C–N bonds in organic molecules, thereby transforming them into other chemical bonds and expanding the utility of thianthracium salts . Thianthrenium salts allows the site- and chemoselective functionalization of chemical bonds without the need for directing groups, establishing them as versatile precursors for various chemical bond formation processes . Recently, Ackermann et al .…”

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confidence: 99%

Palladium(II)-Catalyzed Heck Coupling: Direct Stereoselective Synthesis of C-Aryl Glycosides from Nonactivated Glycals and Thianthrenium Salts

Wei,

Zeng,

et al. 2024

Org. Lett.

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Here, we report an efficient Pd(II)-catalyzed Heck coupling reaction utilizing modular and readily available thianthrenium salts. The tunability and ease of thianthrenium salts facilitated the integration of glycals with drugs, natural products, and peptides. This method allows the incorporation of diverse glycals into structurally varied aglycon components without directing groups or prefunctionalization and provides a practical method for synthesizing C-aryl glycosides, offering a new avenue for the production of complex glycosides with potential applications.

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Unusual Regio‐ and Chemoselectivity in Oxidation of Pyrroles and Indoles Enabled by a Thianthrenium Salt Intermediate

Hann,

Lyall,

Kociok‐Köhn

et al. 2024

Angewandte Chemie

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A dearomative oxidation of pyrroles to Δ3‐pyrrol‐2‐ones is described, which employs a sulfoxide as oxidant, in conjunction with a carboxylic acid anhydride and a Brønsted acid additive. 3‐Substituted pyrroles undergo regioselective oxidation to give the product isomer in which oxygen has been introduced at the more sterically hindered position. This counterintuitive regioselectivity is rationalized by a proposed mechanism that proceeds by initial thianthrenium introduction at the less‐hindered pyrrole α‐position, followed by distal attack of an oxygen nucleophile and subsequent elimination of thianthrene. Furthermore, the same reaction conditions are also able to effect a chemoselective oxidation of indoles to indolin‐3‐ones and additionally of indolin‐3‐ones to 2‐hydroxyindolin‐3‐ones. Here again, the observed regio‐ and chemoselectivities are rationalized through the intermediacy of a thianthrenium salt.

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Nickel-Catalyzed Selective C–H Cyanation via Aromatic Thianthrenium Salts

Cited by 9 publications

References 58 publications

Synthetic Applications of Sulfonium Salts as Aryl Radical Precursors

Synthetic Applications of Sulfonium Salts as Aryl Radical Precursors

Palladium(II)-Catalyzed Heck Coupling: Direct Stereoselective Synthesis of C-Aryl Glycosides from Nonactivated Glycals and Thianthrenium Salts

Unusual Regio‐ and Chemoselectivity in Oxidation of Pyrroles and Indoles Enabled by a Thianthrenium Salt Intermediate

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