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Tandem Iridium-Catalyzed Decarbonylative C-H Activation of Indole: Sacrificial Electron-Rich Ketone-Assisted Bis-arylsulfenylation.

ABSTRACT: Described herein is a decarbonylative tandem C-H bis-arylsulfenylation of indole at the C2 and C4 C-H bonds through the use of pentamethylcyclopentadienyl iridium dichloride dimer ([Cp*IrCl₂]₂) catalyst and disulfides. A new sacrificial electron-rich adamantoyl-directing group facilitates indole C-H bis-functionalization with a traceless in situ removal. Various differently substituted disulfides can be easily accommodated in this reaction by a coordination to Ir(III) through the formation of six- and five-membered iridacycles at the C2 and C4 positions, respectively. Mechanistic studies show that a C-H activation-induced C-C activation is involved in the catalytic cycle.

SUBMITTER: Kathiravan S

PROVIDER: S-EPMC8289288 | biostudies-literature | 2021 May

REPOSITORIES: biostudies-literature

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Tandem Iridium-Catalyzed Decarbonylative C-H Activation of Indole: Sacrificial Electron-Rich Ketone-Assisted Bis-arylsulfenylation.

Kathiravan Subban S Anaspure Prasad P Zhang Tianshu T Nicholls Ian A IA

Organic letters 20210428 9

Described herein is a decarbonylative tandem C-H bis-arylsulfenylation of indole at the C2 and C4 C-H bonds through the use of pentamethylcyclopentadienyl iridium dichloride dimer ([Cp*IrCl<sub>2</sub>]<sub>2</sub>) catalyst and disulfides. A new sacrificial electron-rich adamantoyl-directing group facilitates indole C-H bis-functionalization with a traceless in situ removal. Various differently substituted disulfides can be easily accommodated in this reaction by a coordination to Ir(III) throu ...[more]

PMID: 33908788

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