Oxidative Dearomative Cross-Dehydrogenative Coupling of Indoles with Diverse C-H Nucleophiles: Efficient Approach to 2,2-Disubstituted Indolin-3-ones

The oxidative, dearomative cross-dehydrogenative coupling of indoles with various C-H nucleophiles is developed. This process features a broad substrate scope with respect to both indoles and nucleophiles, affording structurally diverse 2,2-disubstituted indolin-3-ones in high yields (up to 99%). Th...

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Main Authors: Xue Yan, Ying-De Tang, Cheng-Shi Jiang, Xigong Liu, Hua Zhang
Format: Article
Language:English
Published: MDPI AG 2020-01-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/25/2/419
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author Xue Yan
Ying-De Tang
Cheng-Shi Jiang
Xigong Liu
Hua Zhang
author_facet Xue Yan
Ying-De Tang
Cheng-Shi Jiang
Xigong Liu
Hua Zhang
author_sort Xue Yan
collection DOAJ
description The oxidative, dearomative cross-dehydrogenative coupling of indoles with various C-H nucleophiles is developed. This process features a broad substrate scope with respect to both indoles and nucleophiles, affording structurally diverse 2,2-disubstituted indolin-3-ones in high yields (up to 99%). The oxidative dimerization and trimerization of indoles has also been demonstrated under the same conditions.
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spelling doaj.art-c732bb06e0164e799ed3ecc832d4261c2022-12-21T18:27:09ZengMDPI AGMolecules1420-30492020-01-0125241910.3390/molecules25020419molecules25020419Oxidative Dearomative Cross-Dehydrogenative Coupling of Indoles with Diverse C-H Nucleophiles: Efficient Approach to 2,2-Disubstituted Indolin-3-onesXue Yan0Ying-De Tang1Cheng-Shi Jiang2Xigong Liu3Hua Zhang4School of Chemistry and Chemical Engineering, University of Jinan, Jinan 250022, ChinaSchool of Chemistry and Chemical Engineering, University of Jinan, Jinan 250022, ChinaSchool of Biological Science and Technology, University of Jinan, Jinan 250022, ChinaSchool of Biological Science and Technology, University of Jinan, Jinan 250022, ChinaSchool of Biological Science and Technology, University of Jinan, Jinan 250022, ChinaThe oxidative, dearomative cross-dehydrogenative coupling of indoles with various C-H nucleophiles is developed. This process features a broad substrate scope with respect to both indoles and nucleophiles, affording structurally diverse 2,2-disubstituted indolin-3-ones in high yields (up to 99%). The oxidative dimerization and trimerization of indoles has also been demonstrated under the same conditions.https://www.mdpi.com/1420-3049/25/2/419cross couplingdearomatizationc-h functionalizationindolin-3-onesdimerization and trimerization of indoles
spellingShingle Xue Yan
Ying-De Tang
Cheng-Shi Jiang
Xigong Liu
Hua Zhang
Oxidative Dearomative Cross-Dehydrogenative Coupling of Indoles with Diverse C-H Nucleophiles: Efficient Approach to 2,2-Disubstituted Indolin-3-ones
Molecules
cross coupling
dearomatization
c-h functionalization
indolin-3-ones
dimerization and trimerization of indoles
title Oxidative Dearomative Cross-Dehydrogenative Coupling of Indoles with Diverse C-H Nucleophiles: Efficient Approach to 2,2-Disubstituted Indolin-3-ones
title_full Oxidative Dearomative Cross-Dehydrogenative Coupling of Indoles with Diverse C-H Nucleophiles: Efficient Approach to 2,2-Disubstituted Indolin-3-ones
title_fullStr Oxidative Dearomative Cross-Dehydrogenative Coupling of Indoles with Diverse C-H Nucleophiles: Efficient Approach to 2,2-Disubstituted Indolin-3-ones
title_full_unstemmed Oxidative Dearomative Cross-Dehydrogenative Coupling of Indoles with Diverse C-H Nucleophiles: Efficient Approach to 2,2-Disubstituted Indolin-3-ones
title_short Oxidative Dearomative Cross-Dehydrogenative Coupling of Indoles with Diverse C-H Nucleophiles: Efficient Approach to 2,2-Disubstituted Indolin-3-ones
title_sort oxidative dearomative cross dehydrogenative coupling of indoles with diverse c h nucleophiles efficient approach to 2 2 disubstituted indolin 3 ones
topic cross coupling
dearomatization
c-h functionalization
indolin-3-ones
dimerization and trimerization of indoles
url https://www.mdpi.com/1420-3049/25/2/419
work_keys_str_mv AT xueyan oxidativedearomativecrossdehydrogenativecouplingofindoleswithdiversechnucleophilesefficientapproachto22disubstitutedindolin3ones
AT yingdetang oxidativedearomativecrossdehydrogenativecouplingofindoleswithdiversechnucleophilesefficientapproachto22disubstitutedindolin3ones
AT chengshijiang oxidativedearomativecrossdehydrogenativecouplingofindoleswithdiversechnucleophilesefficientapproachto22disubstitutedindolin3ones
AT xigongliu oxidativedearomativecrossdehydrogenativecouplingofindoleswithdiversechnucleophilesefficientapproachto22disubstitutedindolin3ones
AT huazhang oxidativedearomativecrossdehydrogenativecouplingofindoleswithdiversechnucleophilesefficientapproachto22disubstitutedindolin3ones