Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 19, Pages 9231-9245Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo501652w
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Funding
- National Research Foundation of Korea - Korean Government [NRF-2012R1A1A1004077]
- Global Research Network through National Research Foundation of Korea - Korean Government [NRF-2014S1A2A2028156]
- Science Research Center (Center for New Directions in Organic Synthesis) through National Research Foundation of Korea - Korean Government [NRF-2014R1A5A1011165]
- Nanyang Technological University (NTU)
- High Performance Computing Centre at NTU for computer resources
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A straightforward and high-yielding synthesis of 1,4-diaryl-1H-imidazoles is reported. 1,4-Diaryl-1H-imidazoels have been difficult to access in ambient conditions, but our method utilizes two different facets of isocyanide reactivity to achieve it. The reaction is believed to involve (1) NHC-copper-catalyzed isocyanide insertion into alcohol to form an N-arylformimidate intermediate and (2) subsequent base-promoted cycloaddition with benzyl isocyanide derivatives There is cooperation between these two processes through the deprotonation of benzyl isocyanide by KOtBu. The deprotonation gives tert-butyl alcohol and the benzyl isocyanide anion which are used for the first and second steps of the reaction, respectively. Various control and kinetic experiments were carried out to gain an in-depth understanding of the reaction mechanism and isocyanide reactivity. The reaction mechanism determined by density functional theory calculations was consistent with the experimental data and provided detailed explanations for the reactivity trends.
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