An efficient and chemoselective method to generate arynes

Metze, Bryan E.; Roberts, Riley A.; Nilova, Aleksandra; Stuart, David R.

doi:10.1039/d3sc05429b

Chem. Sci.

2023

DOI: 10.1039/d3sc05429b

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An efficient and chemoselective method to generate arynes

Bryan E. Metze,

Riley A. Roberts,

Aleksandra Nilova

et al.

Abstract: A chemoselective method to generate arynes by deprotonation of aryl(Mes)iodonium salts with potassium phosphate has been developed and was shown to be one of the most functional group compatible methods to form these reactive intermediates.

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2024

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Cited by 3 publications

(1 citation statement)

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“…The 3,5-dimethylisoxazol-4-yl (DMIX) group has been recently introduced by Xue and Zhao as an effective auxiliary to provide highly selective aryl transfer in reactions of unsymmetrical diaryliodonium salts . Since then, however, very little research has focused on the exploitation of the potential of this auxiliary in challenging arylation reactions using unsymmetrical diaryliodonium salts with aryl groups of a similar electronic and/or steric nature, when remarkable selectivity issues arise …”

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confidence: 99%

(Indol-3-yl)(DMIX)Iodonium Salts: Novel Electrophilic Indole Reagents

Bugaenko,

Malashchenko,

Kopytov

et al. 2024

Org. Lett.

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A new umpolung approach to the C 3 −H functionalization of indoles with diverse nucleophiles based on the intermediate formation of I(III) reagents is described. The 3,5-dimethylisoxazol-4yl auxiliary allows for selective indole transfer under catalyst-free conditions, which was impossible using previously reported reagents.Combining the mildness of transition-metal-free conditions and the high reactivity of hypervalent iodine reagents, this protocol tolerates various functional groups and provides access to indoles that are difficult to prepare conventionally.

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mentioning

confidence: 99%

(Indol-3-yl)(DMIX)Iodonium Salts: Novel Electrophilic Indole Reagents

Bugaenko,

Malashchenko,

Kopytov

et al. 2024

Org. Lett.

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Basicity‐Controlled Reactivity of meta‐OTf‐Substituted Diaryliodonium Salts for Direct Arylation or Diels‐Alder Cycloaddition of Pyrrole Derivatives

Jiang,

Li,

Wang

et al. 2024

Asian J Org Chem

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In this study, we explored the reactivity of meta‐trifluoromethanesulfonate (OTf) substituted diaryliodonium salts under alkaline conditions. Two distinct pathways with direct arylation of pyrrole derivatives and Diels‐Alder cycloaddition via aryne intermediates, have been found upon the relative alkalinity strength of potassium carbonates or hydroxides. This approach offers a straightforward and efficient route to synthesize heterocyclic aromatics under mild reaction conditions with tolerance of various functional groups.

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Derivatization of 2,1,3-Benzothiadiazole via Regioselective C–H Functionalization and Aryne Reactivity

Kunz,

Barnå,

Urrutia

et al. 2024

J. Org. Chem.

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Despite growing interest in 2,1,3-benzothiadiazole (BTD) as an integral component of many functional molecules, methods for the functionalization of its benzenoid ring have remained limited, and many even simply decorated BTDs have required de novo synthesis. We show that regioselective Ir-catalyzed C−H borylation allows access to versatile 5-boryl or 4,6-diboryl BTD building blocks, which undergo functionalization at the C4, C5, C6, and C7 positions. The optimization and regioselectivity of C−H borylation are discussed. A broad reaction scope is presented, encompassing ipso substitution at the C−B bond, the first examples of ortho-directed C−H functionalization of BTD, ring closing reactions to generate fused ring systems, as well as the generation and capture reactions of novel BTD-based heteroarynes. The regioselectivity of the latter is discussed with reference to the Aryne Distortion Model.

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An efficient and chemoselective method to generate arynes

Abstract: A chemoselective method to generate arynes by deprotonation of aryl(Mes)iodonium salts with potassium phosphate has been developed and was shown to be one of the most functional group compatible methods to form these reactive intermediates.

Cited by 3 publications

References 61 publications

(Indol-3-yl)(DMIX)Iodonium Salts: Novel Electrophilic Indole Reagents

(Indol-3-yl)(DMIX)Iodonium Salts: Novel Electrophilic Indole Reagents

Basicity‐Controlled Reactivity of meta‐OTf‐Substituted Diaryliodonium Salts for Direct Arylation or Diels‐Alder Cycloaddition of Pyrrole Derivatives

Derivatization of 2,1,3-Benzothiadiazole via Regioselective C–H Functionalization and Aryne Reactivity

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