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Organic Iron for the PdCl2/FeCl3-Cocatalyzed Coupling Cyclization of 2,3-Allenoates in the Presence of Allylic Bromides

Authors

  • Bo Chen,

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032 (P. R. China), Fax: (+86)21-6416-7510
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  • Prof. Dr. Shengming Ma

    Corresponding author
    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032 (P. R. China), Fax: (+86)21-6416-7510
    2. Shanghai Key Laboratory of Green Chemistry and Chemical Process, Department of Chemistry, East China Normal University, 3663 North Zhongshan Lu, Shanghai 200062 (P. R. China)
    • State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032 (P. R. China), Fax: (+86)21-6416-7510
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Abstract

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New coupling: The interaction of ferric chloride with 2,3-allenoates generates a 2-(5H)-furanonyl iron species, which was observed to readily undergo transmetalation with PdCl2 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 FeCl3 as the cocatalyst of PdCl2.

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