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A review on the assembly of multi-substituted pyridines via Co-catalyzed [2 + 2 + 2] cycloaddition with nitriles.
Org Biomol Chem. 2022 09 28; 20(37):7391-7404.OB

Abstract

In recent years, many methods for the facile synthesis of pyridines and their derivatives have been developed. The [2 + 2 + 2] cycloaddition reaction of alkynes and nitriles catalyzed by transition metals has emerged as the most straightforward and efficient method to obtain pyridine derivatives. Recently, Earth-abundant cobalt has been employed as a versatile and economical catalyst for the synthesis of functionalized molecules, as compared to other transition metals. This review mainly focuses on the recent research and development of the Co-catalyzed intramolecular [2 + 2 + 2] cycloaddition of diynes-nitriles or intermolecular [2 + 2 + 2] cycloaddition reaction of alkynes or diynes with nitriles for the construction of chiral or achiral multi-substituted pyridines. Meanwhile, brief mechanistic insights are also discussed here to explain the observed regioselectivity.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Cen K
College of Chemistry and Chemical Engineering, University of South China, Hengyang 421001, China. jinhuicai@usc.edu.cn.
Usman M
College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, China.
Shen W
College of Chemistry and Chemical Engineering, University of South China, Hengyang 421001, China. jinhuicai@usc.edu.cn.
Liu M
College of Pharmaceutical Science, University of South China, Hengyang 421001, Hunan, China.
Yang R
College of Chemistry and Chemical Engineering, University of South China, Hengyang 421001, China. jinhuicai@usc.edu.cn.
Cai J
College of Chemistry and Chemical Engineering, University of South China, Hengyang 421001, China. jinhuicai@usc.edu.cn.

MeSH

AlkynesCatalysisCobaltCycloaddition ReactionDiynesNitrilesPyridines

Pub Type(s)

Journal Article
Review
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

36098263

Citation

Cen, Kaili, et al. "A Review On the Assembly of Multi-substituted Pyridines Via Co-catalyzed [2 + 2 + 2] Cycloaddition With Nitriles." Organic & Biomolecular Chemistry, vol. 20, no. 37, 2022, pp. 7391-7404.
Cen K, Usman M, Shen W, et al. A review on the assembly of multi-substituted pyridines via Co-catalyzed [2 + 2 + 2] cycloaddition with nitriles. Org Biomol Chem. 2022;20(37):7391-7404.
Cen, K., Usman, M., Shen, W., Liu, M., Yang, R., & Cai, J. (2022). A review on the assembly of multi-substituted pyridines via Co-catalyzed [2 + 2 + 2] cycloaddition with nitriles. Organic & Biomolecular Chemistry, 20(37), 7391-7404. https://doi.org/10.1039/d2ob01344d
Cen K, et al. A Review On the Assembly of Multi-substituted Pyridines Via Co-catalyzed [2 + 2 + 2] Cycloaddition With Nitriles. Org Biomol Chem. 2022 09 28;20(37):7391-7404. PubMed PMID: 36098263.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A review on the assembly of multi-substituted pyridines via Co-catalyzed [2 + 2 + 2] cycloaddition with nitriles. AU - Cen,Kaili, AU - Usman,Muhammad, AU - Shen,Wangzhen, AU - Liu,Meijing, AU - Yang,Rong, AU - Cai,Jinhui, Y1 - 2022/09/28/ PY - 2022/9/14/pubmed PY - 2022/9/30/medline PY - 2022/9/13/entrez SP - 7391 EP - 7404 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 20 IS - 37 N2 - In recent years, many methods for the facile synthesis of pyridines and their derivatives have been developed. The [2 + 2 + 2] cycloaddition reaction of alkynes and nitriles catalyzed by transition metals has emerged as the most straightforward and efficient method to obtain pyridine derivatives. Recently, Earth-abundant cobalt has been employed as a versatile and economical catalyst for the synthesis of functionalized molecules, as compared to other transition metals. This review mainly focuses on the recent research and development of the Co-catalyzed intramolecular [2 + 2 + 2] cycloaddition of diynes-nitriles or intermolecular [2 + 2 + 2] cycloaddition reaction of alkynes or diynes with nitriles for the construction of chiral or achiral multi-substituted pyridines. Meanwhile, brief mechanistic insights are also discussed here to explain the observed regioselectivity. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/36098263/A_review_on_the_assembly_of_multi_substituted_pyridines_via_Co_catalyzed_[2_+_2_+_2]_cycloaddition_with_nitriles_ DB - PRIME DP - Unbound Medicine ER -