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Tandem Insertion-Cyclization Reaction of Isocyanides in the Synthesis of 1,4-Diaryl-1H-imidazoles: Presence of N-Arylformimidate Intermediate

Benjamin Pooi, Jeongbin Lee, Kyujin Choi, Hajime Hirao* and Soon Hyeok Hong*

*Seoul National University, Seoul 151-747, Republic of Korea; Nanyang Technological University, 637371 Singapore, Email: hiraontu.edu.sg, soonhongsnu.ac.kr

B. Pooi, J. Lee, K. Choi, H. Hirao, S. H. Hong, J. Org. Chem., 2014, 79, 9231-9545.

DOI: 10.1021/jo501652w (free Supporting Information)


Abstract

A NHC-copper-catalyzed isocyanide insertion into alcohol to form an N-arylformimidate intermediate and subsequent base-promoted cycloaddition with benzyl isocyanide derivatives enables a straightforward and high-yielding synthesis of 1,4-diaryl-1H-imidazoles.

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Key Words

imidazoles


ID: J42-Y2014