Synthesis 2016; 48(17): 2781-2788
DOI: 10.1055/s-0035-15661438
special topic
© Georg Thieme Verlag Stuttgart · New York

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

Cheng-Yuan Liu
a  Institute of Chemistry, Academia Sinica, Nangang, Taipei, 11529, Taiwan, ROC   Email: tgong@gate.sinica.edu.tw
,
Ying-Ho Chen
a  Institute of Chemistry, Academia Sinica, Nangang, Taipei, 11529, Taiwan, ROC   Email: tgong@gate.sinica.edu.tw
,
Chih-Hao Chen
a  Institute of Chemistry, Academia Sinica, Nangang, Taipei, 11529, Taiwan, ROC   Email: tgong@gate.sinica.edu.tw
b  Department of Molecular Science and Engineering, National Taipei University of Technology, Taipei, 10608, Taiwan, ROC
,
Ming-Shiuan Yu
a  Institute of Chemistry, Academia Sinica, Nangang, Taipei, 11529, Taiwan, ROC   Email: tgong@gate.sinica.edu.tw
,
Fu-Yu Tsai*
b  Department of Molecular Science and Engineering, National Taipei University of Technology, Taipei, 10608, Taiwan, ROC
,
Tiow-Gan Ong*
a  Institute of Chemistry, Academia Sinica, Nangang, Taipei, 11529, Taiwan, ROC   Email: tgong@gate.sinica.edu.tw
c  Department of Applied Chemistry, National Chiao Tung University, HsinChu, Taiwan, ROC
› Author Affiliations
Further Information

Publication History

Received: 23 February 2016

Accepted after revision: 17 March 2016

Publication Date:
15 June 2016 (eFirst)

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.

Supporting Information

 
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