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Synfacts 2006(12): 1223-1223
DOI: 10.1055/s-2006-955572
DOI: 10.1055/s-2006-955572
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
Titanium-Mediated Synthesis of N-Substituted 2-Arylpyrroles
M. Ohkubo, D. Hayashi, D. Oikawa, K. Fukuhara, S. Okamoto*, F. Sato
Kanagawa University and Tokyo Institute of Technology, Yokohama, Japan
Further Information
Publication History
Publication Date:
22 November 2006 (online)
Significance
A one-pot synthesis of N-substituted 2-arylpyrroles is reported which involves the reaction of arylaldehyde imines with the divalent titanium reagent, Ti(O-i-Pr)4/2i-PrMgCl and the commercially available 3,3-diethoxypropyne. The reaction is proposed to occur via the intermediacy of the (η2-Imine)Ti(O-i-Pr)2 complex 1 and thereby has some similarity to the Kulinkovich reaction in the initial steps. Bromo and trifluoromethyl groups tolerate the reaction conditions; however, aniline and 1-substituted 3,3-diethoxypropyne fail in this reaction.