Copper-catalyzed direct couplings of terminal alkynes with primary and secondary benzyl bromides

Literature Information

Publication Date 2019-04-19
DOI 10.1039/C9QO00335E
Impact Factor 5.281
Authors

Huiru Zhang, Nan Sun, Baoxiang Hu, Zhenlu Shen, Xinquan Hu


View Original

Abstract

We have developed a facile Cu-catalyzed benzylation of terminal alkynes from easily available benzyl bromides. Both primary and secondary benzylic bromides have been successfully coupled with various aryl alkynes, alkyl alkynes and enynes, selectively affording benzyl alkynes in moderate to excellent yields. Examples of scale-up reactions as well as the application for preparing substituted allenes and phenanthrene have further demonstrated the practicality and efficiency of the developed strategy.

Related Literature

Three new conjugated polymers based on benzo[2,1-b:3,4-b′]dithiophene: synthesis, characterization, photoinduced charge transfer and theoretical calculation studies

Shaojie Chen, Qiuyu Zhang, Hepeng Zhang, Junwei Gu, Mingliang Ma, Tiejun Xin, Yanyang Zhou, Jian Zhou, Qing Liu

2012-06-07 Paper

DOI: 10.1039/C2PY20122D

ATRP–RCMpolymercyclization: synthesis of amphiphilic cyclic polystyrene-b-poly(ethylene oxide) copolymers

Eisuke Baba, Satoshi Honda, Takuya Yamamoto, Yasuyuki Tezuka

2011-11-23 Paper

DOI: 10.1039/C1PY00475A

Honeycomb structured polymer films via breath figures

Maribel Hernández-Guerrero, Martina H. Stenzel

2011-11-02 Review Article

DOI: 10.1039/C1PY00219H

Poly(N-isopropylacrylamide) on two-dimensional graphene oxide surfaces

Junjie Qi, Weipeng Lv, Guoliang Zhang, Fengbao Zhang, Xiaobin Fan

2012-01-18 Communication

DOI: 10.1039/C2PY00577H

Controlled grafting of cellulose fibres – an outlook beyond paper and cardboard

Eva Malmström, Anna Carlmark

2011-11-08 Review Article

DOI: 10.1039/C1PY00445J

Front cover

Cover

DOI: 10.1039/C2PY90019J

Tuning the photovoltaic parameters of thiophene-linked donor–acceptor liquid crystalline copolymers for organic photovoltaics

Lie Chen, Fan Li, Xingye Ren, Hongming Wang, Yongfang Li

2012-01-17 Paper

DOI: 10.1039/C2PY00523A

Back cover

Front/Back Matter

DOI: 10.1039/C2PY90013K

One-step RAFT synthesis of well-defined amphiphilic star polymers and their self-assembly in aqueous solution

Christoph Herfurth, Paula Malo de Molina, Christoph Wieland, Sarah Rogers, Michael Gradzielski

2012-04-26 Paper

DOI: 10.1039/C2PY20126G

You might also like

Compound Q&A

Are there alternatives to 1-(4-Chlorophenyl)-N-hydroxymethanimine (CAS: 3848-36-0) in synthesis?

When considering alternatives to 1-(4-Chlorophenyl)-N-hydroxymethanimine (CAS: 3...

3848-36-01-(4-Chlorophenyl)-N...
Compound Q&A

How is 3-(4-Bromophenyl)-5-(2-fluorophenyl)-1,2,4-oxadiazole (CAS: 419553-16-5) typically synthesized?

3-(4-Bromophenyl)-5-(2-fluorophenyl)-1,2,4-oxadiazole is synthesized through a m...

419553-16-53-(4-Bromophenyl)-5-...
Compound Q&A

How is 5-Chloro-2-(4-chlorophenyl)-4-methyl-6-[3-(1-piperidinyl)propoxy]pyrimidine (CAS: 1639220-19-1) typically synthesized?

5-Chloro-2-(4-chlorophenyl)-4-methyl-6-[3-(1-piperidinyl)propoxy]pyrimidine (CAS...

1639220-19-15-Chloro-2-(4-chloro...
Compound Q&A

What industries use 2-Chloro-4-(difluoromethoxy)pyridine (CAS: 1206978-15-5)?

2-Chloro-4-(difluoromethoxy)pyridine is used in the pharmaceutical industry for ...

1206978-15-52-Chloro-4-(difluoro...
Compound Q&A

What regulatory guidelines apply to 3-Chloro-6-methylpyridazine (CAS: 1121-79-5)?

3-Chloro-6-methylpyridazine (CAS: 1121-79-5) is classified under the Globally Ha...

1121-79-53-Chloro-6-methylpyr...
Compound Q&A

Are there alternatives to Methyl 4,5-dimethyl-2-nitrobenzoate in synthesis?

Several alternatives can be used in the synthesis of Methyl 4,5-dimethyl-2-nitro...

90922-74-0Methyl 4,5-dimethyl-...
Compound Q&A

Are there alternatives to (2E,2'E)-3,3'-(1,4-Phenylene)bisacrylaldehyde in synthesis?

Alternatives to (2E,2'E)-3,3'-(1,4-Phenylene)bisacrylaldehyde include other acry...

63405-68-5(2E,2'E)-3,3'-(1,4-P...
Compound Q&A

What is 3-Amino-5-chloropyridin-2-ol hydrochloride (CAS: 1261906-29-9)?

3-Amino-5-chloropyridin-2-ol hydrochloride is an organic compound with the CAS n...

1261906-29-93-Amino-5-chloropyri...
Compound Q&A

What precautions should be taken when handling 6,7-Difluoro-2,3-dihydro-4H-chromen-4-one (CAS: 1092349-93-3)?

When handling 6,7-Difluoro-2,3-dihydro-4H-chromen-4-one, it is essential to wear...

1092349-93-36,7-Difluoro-2,3-dih...

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.