Gold-catalyzed C5-alkylation of indolines and sequential oxidative aromatization: access to C5-functionalized indoles

Literature Information

Publication Date 2018-05-02
DOI 10.1039/C8OB00826D
Impact Factor 3.876
Authors

Wenzheng Zhang, Guangyang Xu, Lin Qiu, Jiangtao Sun


View Original

Abstract

A novel protocol for the synthesis of C5-alkylated indole derivatives via a gold-catalyzed reaction of indolines with diazo compounds and subsequent oxidative aromatization has been developed. C–H bond functionalization selectively occurs at the C5-position of indolines without a directing group. The experimental operation is simple and the whole process can be manipulated in one-pot.

Related Literature

A new trifluoromethylated sulfonamide phosphine ligand for Ag(i)-catalyzed enantioselective [3 + 2] cycloaddition of azomethine ylides

Yuanqi Wu, Bing Xu, Bing Liu, Zhan-Ming Zhang, Yu Liu

2018-12-20 Paper

DOI: 10.1039/C8OB02922A

One-pot stapling of interchain disulfides of antibodies using an isobutylene motif

Shuang Sun, Padma Akkapeddi, Nuria Martínez-Sáez, Vukosava M. Torres, Carlos Cordeiro, Omar Boutureira

2018-12-10 Paper

DOI: 10.1039/C8OB02877J

Applications of N′-monofunctionalised TsDPEN derivatives in asymmetric catalysis

Jonathan Barrios-Rivera, Yingjian Xu, Martin Wills

2019-01-04 Review Article

DOI: 10.1039/C8OB02889C

Front cover

Cover

DOI: 10.1039/C9OB90022E

Synthesis of a non-natural glucose-2-phosphate ester able to dupe the acc system of Agrobacterium fabrum

Si-Zhe Li, Armelle Vigouroux, Mohammed Ahmar, Abbas El Sahili, Laurent Soulère, Laïla Sago, David Cornu, Solange Moréra, Yves Queneau

2019-01-04 Paper

DOI: 10.1039/C8OB03086C

Access to cyano-substituted pyrazolines through copper-catalyzed cascade cyanation/cyclization of unactivated olefins

Fei Meng, Qin Fang, Weidong Yuan, Ning Xu, Shujun Cao, Jianlin Chun, Jie Li, Honglin Zhang, Yingguang Zhu

2020-04-22 Research Article

DOI: 10.1039/D0QO00282H

Sulfur polymer composites as controlled-release fertilisers

Joshua McErlean, Jessica A. Smith, Tom Hasell, Michael V. Perkins

2018-10-05 Paper

DOI: 10.1039/C8OB02130A

Protic additives or impurities promote imine reduction with pinacolborane

Blake S. N. Huchenski, Alexander W. H. Speed

2018-11-06 Paper

DOI: 10.1039/C8OB02330A

Contents list

Front/Back Matter

DOI: 10.1039/D0QO90032J

Inside front cover

Cover

DOI: 10.1039/D0QO90036B

You might also like

Compound Q&A

What industries use (1R,3S)-1,3-Cyclopentanediol (CAS: 16326-97-9)?

(1R,3S)-1,3-Cyclopentanediol finds applications in various industries. In the ph...

16326-97-9(1R,3S)-1,3-Cyclopen...
Compound Q&A

What precautions should be taken when handling N'-[4-(Dimethylamino)phenyl]-N,N-dimethyl-1,4-benzenediamine (CAS: 637-31-0)?

When handling N'-[4-(Dimethylamino)phenyl]-N,N-dimethyl-1,4-benzenediamine, it i...

637-31-0N'-[4-(Dimethylamino...
Compound Q&A

Are there alternatives to 5-(2,4-Difluorophenyl)-2-methoxypyrimidine (CAS: 1352318-16-1) in synthesis?

There are several alternatives to 5-(2,4-Difluorophenyl)-2-methoxypyrimidine in ...

1352318-16-15-(2,4-Difluoropheny...
Compound Q&A

What regulatory guidelines apply to 1-(3-Methoxyphenoxy)propan-2-ol (CAS: 382141-68-6)?

1-(3-Methoxyphenoxy)propan-2-ol (CAS: 382141-68-6) must comply with the Globally...

382141-68-61-(3-Methoxyphenoxy)...
Compound Q&A

Is Tetrodotoxin Citrate (CAS: 18660-81-6) safe?

Tetrodotoxin Citrate is extremely dangerous and should be handled with extreme c...

18660-81-6Tetrodotoxin Citrate
Compound Q&A

What are the main uses of 2-Methyl-2-propanyl [(1R,3S)-3-hydroxycyclopentyl]carbamate (CAS: 225641-84-9)?

2-Methyl-2-propanyl [(1R,3S)-3-hydroxycyclopentyl]carbamate (CAS: 225641-84-9) i...

225641-84-92-Methyl-2-propanyl ...
Compound Q&A

How should waste containing 4-(2-Hydroxyhexafluoroisopropyl)Benzoic Acid (CAS: 16261-80-6) be handled?

Waste containing 4-(2-Hydroxyhexafluoroisopropyl)Benzoic Acid (CAS: 16261-80-6) ...

16261-80-64-(2-Hydroxyhexafluo...
Compound Q&A

How is 2-Methyl-2-proanyl {(2S)-1-[(benzyloxy)amino]-3-hydroxy-3-methyl-1-oxo-2-butanyl}carbamate (CAS: 102507-19-7) typically synthesized?

2-Methyl-2-proanyl {(2S)-1-[(benzyloxy)amino]-3-hydroxy-3-methyl-1-oxo-2-butanyl...

102507-19-72-Methyl-2-propanyl ...
Compound Q&A

What is Benzeneethanamine, α-ethyl-, hydrochloride (1:1) (CAS: 20735-15-3)?

Benzeneethanamine, α-ethyl-, hydrochloride (1:1) is an organic compound with the...

20735-15-3Benzeneethanamine, α...
Compound Q&A

Are there alternatives to 3-{(E)-[4-(Dimethylamino)phenyl]diazenyl}benzoic acid (CAS: 20691-84-3) in synthesis?

In the synthesis of compounds similar to 3-{(E)-[4-(Dimethylamino)phenyl]diazeny...

20691-84-33-{(E)-[4-(Dimethyla...

Source Journal

Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
CiteScore: 3.4
Self-citation Rate: 10.3%
Articles per Year: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.