Issue 11, 2016

Iron-catalyzed decarbonylation initiated [2 + 2 + m] annulation of benzene-linked 1,n-enynes with aliphatic aldehydes

Abstract

An iron-catalyzed decarbonylation initiated [2 + 2 + m] annulation of benzene-linked 1,n-enynes with aliphatic aldehydes has been developed. These divergent annulations allow the one-step and efficient synthesis of various fused- or spiro-polycyclic frameworks. Tertiary aldehydes undergo decarbonylation/β-C(sp3)–H cleavage to afford [2 + 2 + 2] cyclization products, whereas secondary aldehydes undergo decarbonylation/α-C(sp3)–H cleavage to generate [2 + 2 + 1] cyclization products.

Graphical abstract: Iron-catalyzed decarbonylation initiated [2 + 2 + m] annulation of benzene-linked 1,n-enynes with aliphatic aldehydes

Supplementary files

Article information

Article type
Research Article
Submitted
03 Aug 2016
Accepted
29 Aug 2016
First published
30 Aug 2016

Org. Chem. Front., 2016,3, 1509-1513

Iron-catalyzed decarbonylation initiated [2 + 2 + m] annulation of benzene-linked 1,n-enynes with aliphatic aldehydes

L. Lv, X. Bai, X. Yan and Z. Li, Org. Chem. Front., 2016, 3, 1509 DOI: 10.1039/C6QO00429F

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