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Iron‐Catalyzed [2+2+2] Annulation of Aliphatic Bridged 1, n ‐Enynes with Aldehydes for the Synthesis of Fused Pyrans
Author(s) -
Tian Tian,
Wang Xin,
Lv Leiyang,
Li Zhiping
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000653
Subject(s) - annulation , chemistry , catalysis , radical , pyran , benzene , cascade , linker , aldehyde , combinatorial chemistry , organic chemistry , stereochemistry , chromatography , computer science , operating system
An iron‐catalyzed [2+2+2] annulation of aliphatic bridged 1, n ‐enynes with aldehydes was developed. Aldehydes play a dual role as the precursors of acyl radicals to trigger the cascade cyclization but also as the radical acceptors to terminate the annulation. This two‐in‐one strategy overcomes the limitation in [2+2+ m ] cyclization that requires a rigid benzene skeleton as the essential linker, thus enabling the efficient synthesis of functionalized fused [5.6] and [6.6] pyran skeletons.