Literature DB >> 36267892

Synthesis of indoles, indolines, and carbazoles via palladium-catalyzed C─H activation.

Alexander J Rago1, Guangbin Dong1.   

Abstract

The construction of indole, indoline, and carbazole heterocycles has been of significant interest in the synthetic community over the last century due to their prevalence in natural products and other biologically active compounds. In particular for indoles, many conventional methods developed to date require highly pre-functionalized arene precursors, diminishing their attractiveness as "green" syntheses. Carbon-hydrogen bond activation, on the other hand, presents an elegant solution to this problem and can achieve the construction of indoles and their derivatives from comparatively simpler arene precursors. In this short review, we discuss various approaches for preparing indoles, indolines, and carbazoles via palladium-catalyzed C─H bond activation, highlighting their reaction mechanisms and synthetic applications.

Entities:  

Keywords:  1,4-palladium migration; Carbon–carbon bond formation; Carbon–hydrogen bond activation; Carbon–nitrogen bond formation; Heterocycle synthesis; Palladium catalysis; Palladium/norbornene cooperative catalysis

Year:  2021        PMID: 36267892      PMCID: PMC9581343          DOI: 10.1016/j.gresc.2021.02.001

Source DB:  PubMed          Journal:  Green Synth Catal        ISSN: 2666-5549


  37 in total

1.  Exploiting the chemistry of strained rings: synthesis of indoles via domino reaction of aryl iodides with 2H-azirines.

Authors:  David A Candito; Mark Lautens
Journal:  Org Lett       Date:  2010-08-06       Impact factor: 6.005

2.  Applications of vinylogous Mannich reactions. Total syntheses of the Ergot alkaloids rugulovasines A and B and setoclavine.

Authors:  S Liras; C L Lynch; A M Fryer; B T Vu; S F Martin
Journal:  J Am Chem Soc       Date:  2001-06-27       Impact factor: 15.419

3.  Palladium/Norbornene Cooperative Catalysis.

Authors:  Jianchun Wang; Guangbin Dong
Journal:  Chem Rev       Date:  2019-04-25       Impact factor: 60.622

4.  Hydroxylamines As Bifunctional Single-Nitrogen Sources for the Rapid Assembly of Diverse Tricyclic Indole Scaffolds.

Authors:  Liangxin Fan; Jiamao Hao; Jingxun Yu; Xiaojun Ma; Jingjing Liu; Xinjun Luan
Journal:  J Am Chem Soc       Date:  2020-03-27       Impact factor: 15.419

5.  Synthesis of Indoles through Palladium-Catalyzed Three-Component Reaction of Aryl Iodides, Alkynes, and Diaziridinone.

Authors:  Bo Zhou; Zhuo Wu; Ding Ma; Xiaoming Ji; Yanghui Zhang
Journal:  Org Lett       Date:  2018-10-10       Impact factor: 6.005

6.  Carboxylic Acid-Promoted Single-Step Indole Construction from Simple Anilines and Ketones via Aerobic Cross-Dehydrogenative Coupling.

Authors:  Long Ren; Guanglei Nan; Yongcheng Wang; Zhiyan Xiao
Journal:  J Org Chem       Date:  2018-11-13       Impact factor: 4.354

Review 7.  Structurally Modified Norbornenes: A Key Factor to Modulate Reaction Selectivity in the Palladium/Norbornene Cooperative Catalysis.

Authors:  Renhe Li; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2020-10-05       Impact factor: 15.419

Review 8.  C-H alkylation reactions of indoles mediated by Pd(ii) and norbornene: applications and recent developments.

Authors:  Marcus Wegmann; Michael Henkel; Thorsten Bach
Journal:  Org Biomol Chem       Date:  2018-08-01       Impact factor: 3.876

9.  Palladium-Catalyzed [2 + 2 + 1] Annulation of Alkyne-Tethered Aryl Iodides with Diaziridinone: Synthesis of 3,4-Fused Tricyclic Indoles.

Authors:  Lei Zhang; Junyu Chen; Tianshuo Zhong; Xiangyun Zheng; Jian Zhou; Xinpeng Jiang; Chuanming Yu
Journal:  J Org Chem       Date:  2020-08-13       Impact factor: 4.354

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