Pseudocyclic Arylbenziodoxaboroles as Water-Triggered Aryne Precursors in Reactions with Organic Sulfides

Yoshimura, Akira; Ngo, Kim; Mironova, Irina A.; Gardner, Zachary S.; Rohde, Gregory T.; Ogura, Nami; Ueki, Akiharu; Yusubov, Mekhman S.; Saito, Akio; Zhdankin, Viktor V.

doi:10.1021/acs.orglett.4c00197

Org. Lett.

2024

DOI: 10.1021/acs.orglett.4c00197

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Pseudocyclic Arylbenziodoxaboroles as Water-Triggered Aryne Precursors in Reactions with Organic Sulfides

Akira Yoshimura,

Kim Ngo,

Irina A. Mironova

et al.

Abstract: Pseudocyclic arylbenziodoxaboroles are unique aryne precursors under neutral aqueous conditions that selectively react with organic sulfides, forming the corresponding sulfonium salts. This reaction is compatible with various substituents (alkyl, halogen, CN, NO 2 , CHO, and cyclopropyl) in the aromatic ring or alkyl group of the sulfide. Similar reactions of sulfoxides afford ohydroxy-substituted sulfonium salts. The structures of key products were confirmed by X-ray analysis.

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Cited by 2 publications

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Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents

Yoshimura,

Zhdankin

2024

Chem. Rev.

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Hypervalent iodine(III) compounds have found wide application in modern organic chemistry as environmentally friendly reagents and catalysts. Hypervalent iodine reagents are commonly used in synthetically important halogenations, oxidations, aminations, heterocyclizations, and various oxidative functionalizations of organic substrates. Iodonium salts are important arylating reagents, while iodonium ylides and imides are excellent carbene and nitrene precursors. Various derivatives of benziodoxoles, such as azidobenziodoxoles, trifluoromethylbenziodoxoles, alkynylbenziodoxoles, and alkenylbenziodoxoles have found wide application as group transfer reagents in the presence of transition metal catalysts, under metal-free conditions, or using photocatalysts under photoirradiation conditions. Development of hypervalent iodine catalytic systems and discovery of highly enantioselective reactions using chiral hypervalent iodine compounds represent a particularly important recent achievement in the field of hypervalent iodine chemistry. Chemical transformations promoted by hypervalent iodine in many cases are unique and cannot be performed by using any other common, non-iodine-based reagent. This review covers literature published mainly in the last 7−8 years, between 2016 and 2024.

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Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents

Yoshimura,

Zhdankin

2024

Chem. Rev.

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Metal-Free Synthesis of Benzisoxazolones Utilizing ortho-Ester and ortho-Cyano-Functionalized Diaryliodonium Salts with Protected Hydroxylamines

Elboray,

Bae,

Kikushima

et al. 2024

J. Org. Chem.

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Herein, we report the development of metal-free one/two-pot procedures for the synthesis of benzo[c]isoxazol-3(1H)-one (benzisoxazolone) heterocycles by designing diaryliodonium salts featuring ortho-ester or nitrile functional groups. These react smoothly with protected hydroxylamines under mild conditions to produce N-arylhydroxylamine intermediates, which readily cyclize to give benzisoxazolone derivatives under acidic conditions. This metal-free process maintains the weak N−O bond, tolerates a wide range of diaryliodonium salts and protected hydroxylamines with diverse functional/ protecting groups, thereby overcoming the challenges associated with previous transformations. The protocol expands the reaction scope and broadens the chemical space of the fused isoxazolone backbones to include unprecedented five-membered heteroaryl-fused isoxazolones in high yields. This method is also applicable to gram-scale synthesis, and the resulting benzisoxazolones can be effectively derivatized at the N-position to afford valuable compounds.

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Pseudocyclic Arylbenziodoxaboroles as Water-Triggered Aryne Precursors in Reactions with Organic Sulfides

Cited by 2 publications

References 23 publications

Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents

Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents

Metal-Free Synthesis of Benzisoxazolones Utilizing ortho-Ester and ortho-Cyano-Functionalized Diaryliodonium Salts with Protected Hydroxylamines

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