Cyanation with isocyanides: recent advances and perspectives

Shan, Yingying; Zhang, Xiuhua; Liu, Gongle; Li, Jianming; Liu, Yongwei; Wang, Jia; Chen, Dianpeng

doi:10.1039/d3cc05880h

Chem. Commun.

2024

DOI: 10.1039/d3cc05880h

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Cyanation with isocyanides: recent advances and perspectives

Yingying Shan,

Xiuhua Zhang,

Gongle Liu

et al.

Abstract: Cyanations have attracted considerable attentions in organic synthesis for the fact that nitriles are key structural motifs in numerous important dyes, agrochemicals, natural products and drug molecules. As the fourth...

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Cited by 6 publications

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Ligand‐Enabled Gold‐Catalyzed Cyanation of Organohalides

Kumar,

Bhattacharya,

Mane

et al. 2024

Angewandte Chemie

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Herein, we disclose the first report on gold‐catalyzed C(sp2)‐CN cross‐coupling reaction by employing a ligand‐enabled Au(I)/Au(III) redox catalysis. This transformation utilizes acetone cyanohydrin as a nucleophilic cyanide source to convert simple aryl and alkenyl iodides into the corresponding nitriles. Combined experimental and computational studies highlighted the crucial role of cationic silver salts in activating the stable (P,N)‐AuCN complex towards the oxidative addition of aryl iodides to subsequently generate key aryl‐Au(III) cyanide complexes.

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Ligand‐Enabled Gold‐Catalyzed Cyanation of Organohalides

Kumar,

Bhattacharya,

Mane

et al. 2024

Angewandte Chemie

View full text Add to dashboard Cite

show abstract

Ligand‐Enabled Gold‐Catalyzed Cyanation of Organohalides

Kumar,

Bhattacharya,

Mane

et al. 2024

Angew Chem Int Ed

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Electrophile-Controlled Regiodivergent Palladium-Catalyzed Imidoylative Spirocyclization of Cyclic Alkenes

Ding,

Pu,

Lin

et al. 2024

Org. Lett.

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An intermolecular controllable Pd-catalyzed spirocyclization of isocyano cycloalkenes has been developed, offering efficient and selective approaches toward spirocyclic hydropyrrole scaffolds. 2-Azaspiro-1,7-dienes could be obtained through a "chain-walking" process with aryl/vinyl iodides as electrophiles, while the normal Heck product 2-azaspiro-1,6-dienes were selectively generated when aryl triflates were used as the coupling partner of isocyanides. Mechanistic studies suggested that the counteranion of the Pd(II) intermediate played a crucial role in the regioselectivity control. Dihydropyrrole-fused 5,6,7-membered spirocycles were switchably accessed under mild conditions with wide functional group tolerance.

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Cyanation with isocyanides: recent advances and perspectives

Abstract: Cyanations have attracted considerable attentions in organic synthesis for the fact that nitriles are key structural motifs in numerous important dyes, agrochemicals, natural products and drug molecules. As the fourth...

Cited by 6 publications

References 111 publications

Ligand‐Enabled Gold‐Catalyzed Cyanation of Organohalides

Ligand‐Enabled Gold‐Catalyzed Cyanation of Organohalides

Ligand‐Enabled Gold‐Catalyzed Cyanation of Organohalides

Electrophile-Controlled Regiodivergent Palladium-Catalyzed Imidoylative Spirocyclization of Cyclic Alkenes

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