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(1‐Alkynyl)dicarbonylcyclopentadienyliron Complexes as Electron‐Rich Alkynes in Organic Synthesis: BF 3 ‐Mediated [2+2] Cycloaddition/Ring‐Opening Providing (2‐Alkenyl‐1‐imino)iron Complexes
Author(s) -
Nakaya Ryotaro,
Yasuda Shigeo,
Yorimitsu Hideki,
Oshima Koichiro
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201100669
Subject(s) - cycloaddition , chemistry , ring (chemistry) , yield (engineering) , aldehyde , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis , materials science , metallurgy
Strike while the iron is hot! A BF 3 ‐mediated formal [2+2] cycloaddition between (1‐alkynyl)iron complexes and aromatic aldehyde imines occurs, which is followed by ring‐opening of the initially formed azacyclobutenes to yield (2‐alkenyl‐1‐imino)iron complexes (see scheme). The resulting iron complexes undergo deferric substitution reactions with water under oxidative conditions to afford the corresponding cinnamamides with high E selectivity.