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Synfacts 2006(12): 1213-1213
DOI: 10.1055/s-2006-955571
DOI: 10.1055/s-2006-955571
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
Rhenium-Catalyzed Synthesis of Isobenzofurans
Y. Kuninobu*, Y. Nishina, C. Nakagawa, K. Takai*
Okayama University, Japan
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. November 2006 (online)
Significance
A rhenium-catalyzed synthesis of isobenzofurans from aldehydes and ketimines is reported. The reaction occurs by a sequential aromatic C-H activation, aldehyde insertion, cyclization and amine elimination to afford the isobenzofuran derivatives in good yields. The scope was not widely tested: benzaldehydes bearing electron-donating or -withdrawing groups and cinnamaldehyde participated well in the reaction. More interestingly, a one-pot procedure involving trapping of the isobenzofurans in inter- or intramolecular Diels-Alder reaction was also reported.