Copper(i)-catalyzed cycloaddition of silver acetylides and azides: Incorporation of volatile acetylenes into the triazole core

Literature Information

Publication Date 2011-06-03
DOI 10.1039/C1OB05360D
Impact Factor 3.876
Authors

Ilaria Proietti Silvestri, Fikre Andemarian, George N. Khairallah, Su Wan Yap, Tim Quach, Sammi Tsegay, Craig M. Williams, Richard A. J. O'Hair, Paul S. Donnelly, Spencer J. Williams


View Original

Abstract

Silver acetylides and organic azides react under copper(I) catalysis to afford 1,4-disubstituted 1,2,3-triazoles. Mechanistic studies implicate a process involving transmetallation to copper acetylides prior to cycloaddition. This work demonstrates that silver acetylides serve as suitable precursors for entry into copper-mediated coupling reactions. This methodology allows the incorporation of volatile and difficult-to-handle acetylenes into the triazole core.

Related Literature

Organic analysis

Other

DOI: 10.1039/AN8992400288

Trimetallic CoFeCr hydroxide electrocatalysts synthesized at a low temperature for accelerating water oxidation via tuning the electronic structure of active sites

Yibin Yang, Xun Cui, Di Gao, Huichao He, Yingqing Ou, Ming Zhou, Qingxin Lai, Xijun Wei, Peng Xiao, Yunhuai Zhang

2020-05-08 Paper

DOI: 10.1039/D0SE00659A

Synthesis and electrochemical performance of Co1−xNixS QDs as electrode materials for high performance supercapacitors

Mingyan Chuai, Hongpeng Zhang, Yu Tong, Kewei Zhang, Mingzhe Zhang

2020-04-24 Paper

DOI: 10.1039/D0SE00366B

Front cover

Cover

DOI: 10.1039/C4BM90035A

Review

Other

DOI: 10.1039/AN8992400308

A novel nonheme manganese(ii) complex for (electro) catalytic oxidation of water

Dattaprasad D. Narulkar, Anil Kumar U., Sunder N. Dhuri, Anil Kumar Vardhaman

2020-03-12 Communication

DOI: 10.1039/D0SE00232A

Measuring estriol and estrone simultaneously in liquid cosmetic samples using second-order calibration coupled with excitation–emission matrix fluorescence based on region selection

De-Zhu Tu, Hai-Long Wu, Yuan-Na Li, Juan Zhang, Yong Li, Chong-Chong Nie, Xiao-Hua Zhang, Ru-Qin Yu

2011-11-23 Paper

DOI: 10.1039/C1AY05388D

Reviews

Other

DOI: 10.1039/AN8992400278

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.