Enynone-enabled migratory insertion and Schmittel cyclization cascade for the synthesis of furan-fused fluorenes

Literature Information

Publication Date 2019-02-21
DOI 10.1039/C9QO00045C
Impact Factor 5.281
Authors

He Zhang, Tongxiang Cao, Hejiang Luo, Lianfen Chen, Shifa Zhu


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Abstract

A new method for the synthesis of furan-/benzo-fused fluorenes through copper(I)-catalyzed coupling of conjugated enynones or α-diazocarbonyl compounds with dialkynylbenzenes has been developed. This process includes 5-exo-dig cyclization, carbene migratory insertion, Schmittel cyclization and 1,5-H transfer. The obvious advantages of wide substrate scopes, mild reaction conditions, and high atom efficiency make this system highly appealing for the construction of six-substituted benzofuran-embedded fluorenes in a one-pot manner.

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