Rh-Catalyzed nitrene alkyne metathesis/formal C–N bond insertion cascade: synthesis of 3-iminoindolines

Literature Information

Publication Date 2020-04-08
DOI 10.1039/D0QO00294A
Impact Factor 5.281
Authors

Kemiao Hong, Su Zhou, Wenhao Hu


View Original

Abstract

A Rh2(esp)2 catalyzed nitrene/alkyne metathesis (NAM) cascade reaction of alkyne-tethered sulfamates has been developed, which provides facile access to the tricyclic 3-iminoindolines in good to excellent yields with broad substrate scope. The reaction is initiated by a Rh-promoted nitrene/alkyne metathesis (NAM) under oxidative conditions to form the key α-imino metal carbene intermediate, followed by a formal carbene insertion reaction of the amide C–N bond via a Stevens [1,2]-acyl shift.

Related Literature

Peptides and Proteins, RSC Tutorial Chemistry Texts

2003-10-06 Book Review

DOI: 10.1039/B301929M

Index pages

Paper

DOI: 10.1039/NP98401000I1

Ultrasensitive detection of H. pylori in human feces based on immunomagnetic bead capture and fluorescent quantum dots

Lili Chen, Xiangguang Li, Tongda Zou, Tiantian Wang, Xiping Cui, Yingshan Chen, Chunguo Zhang, Suqing Zhao

2019-05-09 Paper

DOI: 10.1039/C9AN00193J

A SERS approach for rapid detection of microRNA-17 in the picomolar range

Monika Schechinger, Haley Marks, Samuel Mabbott, Mahua Choudhury

2019-05-30 Paper

DOI: 10.1039/C9AN00653B

Embedding cyclic nitrone in mesoporous silica particles for EPR spin trapping of superoxide and other radicals

Eric Besson, Stéphane Gastaldi, Emily Bloch, Selma Aslan, Hakim Karoui, Olivier Ouari, Micael Hardy

2019-06-03 Paper

DOI: 10.1039/C9AN00468H

Front cover

Cover

DOI: 10.1039/C8AN90058B

Electronically-tuned triarylmethine scaffolds for fast and continuous monitoring of H2S levels in biological samples

Ramshad Kalluruttimmal, Divya Thekke Thattariyil, Archana Panthalattu Parambil, Ashis Kumar Sen, Lakshmi Chakkumkumarath, Muraleedharan Kannoth Manheri

2019-05-28 Paper

DOI: 10.1039/C9AN00522F

The mechanism and regularity of quenching the effect of bases on fluorophores: the base-quenched probe method

Huihui Mao, Guanghua Luo, Yuxia Zhan, Jun Zhang, Shuang Yao, Yang Yu

2018-04-09 Paper

DOI: 10.1039/C8AN00116B

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 Chemistry Frontiers

Organic Chemistry Frontiers
CiteScore: 7.8
Self-citation Rate: 8.7%
Articles per Year: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

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.