Selective C(8)–H Activation of Imidazopyridines Mediated by Cooperative Nickel–Aluminum Catalysis

Cheng-Yuan Liu; Ying-Ho Chen; Chih-Hao Chen; Ming-Shiuan Yu; Fu-Yu Tsai; Tiow-Gan Ong

doi:10.1055/s-0035-15661438

Synthesis, Table of Contents

Synthesis 2016; 48(17): 2781-2788
DOI: 10.1055/s-0035-15661438

special topic

Selective C(8)–H Activation of Imidazopyridines Mediated by Cooperative Nickel–Aluminum Catalysis

Cheng-Yuan Liu

^aInstitute of Chemistry, Academia Sinica, Nangang, Taipei, 11529, Taiwan, ROC Email: tgong@gate.sinica.edu.tw

,

Ying-Ho Chen

^aInstitute of Chemistry, Academia Sinica, Nangang, Taipei, 11529, Taiwan, ROC Email: tgong@gate.sinica.edu.tw

,

Chih-Hao Chen

^aInstitute of Chemistry, Academia Sinica, Nangang, Taipei, 11529, Taiwan, ROC Email: tgong@gate.sinica.edu.tw

^bDepartment of Molecular Science and Engineering, National Taipei University of Technology, Taipei, 10608, Taiwan, ROC

,

Ming-Shiuan Yu

^aInstitute of Chemistry, Academia Sinica, Nangang, Taipei, 11529, Taiwan, ROC Email: tgong@gate.sinica.edu.tw

,

Fu-Yu Tsai*

^bDepartment of Molecular Science and Engineering, National Taipei University of Technology, Taipei, 10608, Taiwan, ROC

,

Tiow-Gan Ong*

^aInstitute of Chemistry, Academia Sinica, Nangang, Taipei, 11529, Taiwan, ROC Email: tgong@gate.sinica.edu.tw

^cDepartment of Applied Chemistry, National Chiao Tung University, HsinChu, Taiwan, ROC

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Abstract

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This work is dedicated to the victims of the recent Tainan earthquake.

Abstract

A catalytic paradigm is described featuring a synergistic interaction between nickel, aluminum and different ligands to impart a rather remote C–H alkenylation of imidazo[1,5-a]pyridines at the C-8 position without the necessity of installing a directing group. The scope of the direct C–H activation reactions of various 5-aryl- and 3-arylimidazopyridines is established using different sterically hindered alkynes.

Key words

C–H activation - nickel - aluminum - imidazopyridines - cooperative catalysis

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References

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Supplementary Material

Supporting Information