Tandem addition/cyclization for synthesis of 2-aroyl benzofurans and 2-aroyl indoles by carbopalladation of nitriles

Literature Information

Publication Date 2019-12-13
DOI 10.1039/C9OB02408E
Impact Factor 3.876
Authors

Julin Gong, Kun Hu, Yinlin Shao, Renhao Li, Yetong Zhang, Maolin Hu, Jiuxi Chen


View Original

Abstract

The first example of the palladium-catalyzed tandem addition/cyclization of 2-(2-acylphenoxy)acetonitriles with arylboronic acids has been developed, providing a new strategy for the synthesis of 2-aroyl benzofurans with excellent chemoselectivity and wide functional group compatibility. Preliminary mechanistic experiments indicate that this tandem process involves sequential nucleophilic addition generating 2-(2-acylphenoxy)-1-phenylethan-1-one followed by an intramolecular cyclization. This methodology has also been applied to the synthesis of 2-aroyl indoles and the potent CYP19 inhibitor 1-(benzofuran-2-yl(phenyl)methyl)-1H-1,2,4-triazole.

Related Literature

Stability and synthesis across barium tin sulfide material space

Andriy Zakutayev

2023-11-10 Paper

DOI: 10.1039/D3TA04431A

siRNA-loaded DNA nanostructures restore endothelial leakiness

Arun Richard Chandrasekaran

2023-10-04 Editorial

DOI: 10.1039/D3NH90040A

NIR-activated quercetin-based nanogels embedded with CuS nanoclusters for the treatment of drug-resistant biofilms and accelerated chronic wound healing

Amit Nain, Yu-Ting Tseng, Akash Gupta, Yu-Feng Lin, Sangili Arumugam, Yu-Fen Huang

2023-09-19 Communication

DOI: 10.1039/D3NH00275F

MnP4 electrode for Na-ion batteries: a complex and effective electrochemical mechanism

Julien Fullenwarth, Bernard Fraisse, Nicolas Dupré

2023-10-02 Paper

DOI: 10.1039/D3TA02329J

The intrinsic activity descriptor of TM-N3-C single-atom catalysts for electrochemical CO2 reduction: a DFT study

Linmeng Wang, Zhiyuan Liu, Rushuo Li, Ping Yang, Wei Wang, Xiangdong Xue, Shihao Feng, Lingjing Yu, Ge Wang

2023-10-27 Paper

DOI: 10.1039/D3TA04806C

Chemistry and bioactivity of lindenane sesquiterpenoids and their oligomers

Jun Luo, Danyang Zhang, Pengfei Tang, Nan Wang, Shuai Zhao, Lingyi Kong

2023-10-04 Review Article

DOI: 10.1039/D3NP00022B

Active sites of NO selective catalytic reduction over V2O5–WO3/TiO2

Dongrun Xu, Weiye Qu, Junhong Liu, Junxiao Chen, Xue Fang, Liwei Chen, Xi Liu, Yaxin Chen

2023-10-26 Paper

DOI: 10.1039/D3TA05525F

A functional electrolyte containing propyl 4-methylbenzene sulfonate (PMBS) additive to improve the cycling performance of the LiNi0.8Co0.1Mn0.1O2/graphite full cell under the low temperature of −10 °C

Haijia Li, Jian Cai, Jianping Liao, Yiting Li, Xueyi Zeng, Xin He, Chaojun Fan, Zhen Ma, Junmin Nan

2023-11-10 Paper

DOI: 10.1039/D3TA04535H

You might also like

Compound Q&A

What regulatory guidelines apply to 6-Bromo-2-methylimidazo[1,2-a]pyrimidine (CAS: 1111638-05-1)?

6-Bromo-2-methylimidazo[1,2-a]pyrimidine (CAS: 1111638-05-1) falls under various...

1111638-05-16-Bromo-2-methylimid...
Compound Q&A

Are there alternatives to 1-Pyrrolidineethanol, β-methyl-α-phenyl-, (αS,βR) (CAS: 123620-80-4) in synthesis?

While there are no direct alternatives, similar compounds like 1-Pyrrolidineetha...

123620-80-41-Pyrrolidineethanol...
Compound Q&A

Is 4-Methyl-2,6-bis(2-methyl-2-propanyl)phenyl methylcarbamate (CAS: 1918-11-2) safe?

4-Methyl-2,6-bis(2-methyl-2-propanyl)phenyl methylcarbamate (CAS: 1918-11-2) is ...

1918-11-24-Methyl-2,6-bis(2-m...
Compound Q&A

How should 2-(3-Bromo-4-fluorophenyl)-1,3-dioxolane (CAS: 77771-04-1) be stored?

2-(3-Bromo-4-fluorophenyl)-1,3-dioxolane (CAS: 77771-04-1) should be stored in a...

77771-04-12-(3-Bromo-4-fluorop...
Compound Q&A

What are the physical and chemical properties of 4,5,6,7-Tetrahydro-1H-indazole hydrochloride (CAS: 18161-11-0)?

4,5,6,7-Tetrahydro-1H-indazole hydrochloride is a white crystalline solid with a...

18161-11-04,5,6,7-Tetrahydro-1...
Compound Q&A

What is (2R)-1-Methoxy-3-phenyl-2-propanamine (CAS: 59919-07-2)?

(2R)-1-Methoxy-3-phenyl-2-propanamine is a chiral organic compound with the CAS ...

59919-07-2(2R)-1-Methoxy-3-phe...
Compound Q&A

What industries use Ethyl 1-(1-phenylethyl)-1H-imidazole-5-carboxylate (CAS: 56649-47-9)?

Ethyl 1-(1-phenylethyl)-1H-imidazole-5-carboxylate is used in various industries...

56649-47-9Ethyl 1-(1-phenyleth...
Compound Q&A

What regulatory guidelines apply to 4-[(1E,3S)-1-(4-Hydroxyphenyl)-1,4-pentadien-3-yl]phenol (CAS: 17676-24-3)?

4-[(1E,3S)-1-(4-Hydroxyphenyl)-1,4-pentadien-3-yl]phenol (CAS: 17676-24-3) falls...

17676-24-34-[(1E,3S)-1-(4-Hydr...
Compound Q&A

What industries use (S)-3-Amino-5-phenylpentanoic acid hydrochloride (CAS: 331846-97-0)?

(S)-3-Amino-5-phenylpentanoic acid hydrochloride is primarily used in the pharma...

331846-97-0(S)-3-Amino-5-phenyl...
Compound Q&A

How is 7-methoxy-1-benzothiophene-2-carboxylic acid (CAS: 88791-07-5) typically synthesized?

7-Methoxy-1-benzothiophene-2-carboxylic acid is typically synthesized by reactin...

88791-07-57-methoxy-1-benzothi...

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.