Ru(II)-Catalyzed\nSkeletal Editing of Oxindole with\nInternal Alkyne To Synthesize C7-Alkylated Indole Derivatives

A Ru(II)-catalyzed skeletal editing\nof oxindole scaffolds\nwas established\nto afford C7-alkyl acetate indole derivatives using internal alkyne\nand alkyl alcohol. The developed method is simple, efficient, and\nstraightforward. The reaction was extended to substrates having wide\nchemoselective profiles. When unsymmetrical alkynes were used, promising\nregioselectivity was realized. A preliminary mechanistic study revealed\nthat the reaction pathway proceeded by Ru(II)/Ag(I)-catalyzed amide\ncleavage and subsequent oxidative annulation.

Publication Details

Journal
Figshare
Published
2024-09-16
DOI
https://doi.org/10.1021/acs.orglett.4c02870.s001
Primary Topic
Mycorrhizal Fungi and Plant Interactions
Type
article
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article

Ru(II)-Catalyzed\nSkeletal Editing of Oxindole with\nInternal Alkyne To Synthesize C7-Alkylated Indole Derivatives

Figshare
Mycorrhizal Fungi and Plant Interactions
article

Ru(II)-Catalyzed\nSkeletal Editing of Oxindole with\nInternal Alkyne To Synthesize C7-Alkylated Indole Derivatives

article en

Abstract

A Ru(II)-catalyzed skeletal editing\nof oxindole scaffolds\nwas established\nto afford C7-alkyl acetate indole derivatives using internal alkyne\nand alkyl alcohol. The developed method is simple, efficient, and\nstraightforward. The reaction was extended to substrates having wide\nchemoselective profiles. When unsymmetrical alkynes were used, promising\nregioselectivity was realized. A preliminary mechanistic study revealed\nthat the reaction pathway proceeded by Ru(II)/Ag(I)-catalyzed amide\ncleavage and subsequent oxidative annulation.

Figshare
Clean water and sanitation
Openalex Percentile: Top 66%
Mycorrhizal Fungi and Plant Interactions
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Ru(II)-Catalyzed\nSkeletal Editing of Oxindole with\nInternal Alkyne To Synthesize C7-Alkylated Indole Derivatives · Figshare (2024) | TGRS Research Map | TGRS