Organic Iron for the PdCl 2 /FeCl 3 ‐Cocatalyzed Coupling Cyclization of 2,3‐Allenoates in the Presence of Allylic Bromides | Zendy

Chen Bo | Zendy; Ma Shengming | Zendy

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Organic Iron for the PdCl 2 /FeCl 3 ‐Cocatalyzed Coupling Cyclization of 2,3‐Allenoates in the Presence of Allylic Bromides

Author(s) -

Chen Bo,

Ma Shengming

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.201002553

Subject(s) - allylic rearrangement , transmetalation , ferric , coupling (piping) , chemistry , chloride , reagent , medicinal chemistry , organic chemistry , catalysis , materials science , metallurgy

New coupling : The interaction of ferric chloride with 2,3‐allenoates generates a 2‐(5 H )‐furanonyl iron species, which was observed to readily undergo transmetalation with PdCl 2 to result in coupling with allylic bromides (see scheme). Based on this reaction, an efficient method for the synthesis of β‐allyl polysubstituted butenolides from the easily available allylic bromides and 2,3‐allenoates has been developed by using the cheap and readily available FeCl 3 as the cocatalyst of PdCl 2 .

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