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Nickel-Catalyzed [2+2+2] Cycloaddition of Alkyne-Nitriles with Alkynes Assisted by Lewis Acids: Efficient Synthesis of Fused Pyridines.
Chemistry. 2016 Nov 14; 22(47):16765-16769.C

Abstract

A Ni/BPh3 catalyzed [2+2+2] cycloaddition of alkyne-nitriles with alkynes has been developed, which provides an efficient route to fused pyridines under mild reaction conditions. Mechanistic studies indicate that an azanickelacycle via heterocoupling of an alkyne with a nitrile moiety is possibly formed as a key reaction intermediate. The Lewis acid catalyst is crucial to the successful transformation, which is suggested to promote the oxidative cyclization process.

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Authors+Show Affiliations

You X
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, P. R. China.
Xie X
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, P. R. China.
Wang G
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, P. R. China.
Xiong M
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, P. R. China.
Sun R
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, P. R. China.
Chen H
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, P. R. China.
Liu Y
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, P. R. China.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

27643803

Citation

You, Xu, et al. "Nickel-Catalyzed [2+2+2] Cycloaddition of Alkyne-Nitriles With Alkynes Assisted By Lewis Acids: Efficient Synthesis of Fused Pyridines." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 22, no. 47, 2016, pp. 16765-16769.
You X, Xie X, Wang G, et al. Nickel-Catalyzed [2+2+2] Cycloaddition of Alkyne-Nitriles with Alkynes Assisted by Lewis Acids: Efficient Synthesis of Fused Pyridines. Chemistry. 2016;22(47):16765-16769.
You, X., Xie, X., Wang, G., Xiong, M., Sun, R., Chen, H., & Liu, Y. (2016). Nickel-Catalyzed [2+2+2] Cycloaddition of Alkyne-Nitriles with Alkynes Assisted by Lewis Acids: Efficient Synthesis of Fused Pyridines. Chemistry (Weinheim an Der Bergstrasse, Germany), 22(47), 16765-16769. https://doi.org/10.1002/chem.201603829
You X, et al. Nickel-Catalyzed [2+2+2] Cycloaddition of Alkyne-Nitriles With Alkynes Assisted By Lewis Acids: Efficient Synthesis of Fused Pyridines. Chemistry. 2016 Nov 14;22(47):16765-16769. PubMed PMID: 27643803.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Nickel-Catalyzed [2+2+2] Cycloaddition of Alkyne-Nitriles with Alkynes Assisted by Lewis Acids: Efficient Synthesis of Fused Pyridines. AU - You,Xu, AU - Xie,Xin, AU - Wang,Gaonan, AU - Xiong,Meijun, AU - Sun,Renhong, AU - Chen,Haoyi, AU - Liu,Yuanhong, Y1 - 2016/10/10/ PY - 2016/08/11/received PY - 2016/9/20/pubmed PY - 2016/9/20/medline PY - 2016/9/20/entrez KW - alkynes KW - cycloaddition KW - nickel KW - nitriles KW - pyridines SP - 16765 EP - 16769 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 22 IS - 47 N2 - A Ni/BPh3 catalyzed [2+2+2] cycloaddition of alkyne-nitriles with alkynes has been developed, which provides an efficient route to fused pyridines under mild reaction conditions. Mechanistic studies indicate that an azanickelacycle via heterocoupling of an alkyne with a nitrile moiety is possibly formed as a key reaction intermediate. The Lewis acid catalyst is crucial to the successful transformation, which is suggested to promote the oxidative cyclization process. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/27643803/Nickel_Catalyzed_[2+2+2]_Cycloaddition_of_Alkyne_Nitriles_with_Alkynes_Assisted_by_Lewis_Acids:_Efficient_Synthesis_of_Fused_Pyridines_ DB - PRIME DP - Unbound Medicine ER -