Palladium(0)-catalyzed cyclization reaction of polymer-supported aryl iodides with 1,2-allenyl carboxylic acids. A facile solid-phase synthesis of butenolides.
[reaction--see text] Aryl iodides anchored to Merrifield resin via the linkages between a carboxyl, hydroxyl, or hydroxymethyl group and the benzylic chloride moiety in the resin reacted efficiently with 1,2-allenic carboxylic acids under the catalysis of Pd(0) to afford polymer-supported butenolides. Polysubstituted butenolides can be easily cleaved from the resins by Lewis acid-catalyzed processes in good yields and purities.
Ma
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Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. China. masm@pub.sioc.ac.cn
Duan
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Shi
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D015107:4-Butyrolactone / Q000031:analogs & derivatives; D000475:Alkenes / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D015195:Drug Design; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007454:Iodides / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010165:Palladium; D013329:Structure-Activity Relationship
D000475:Alkenes; D002264:Carboxylic Acids; D005663:Furans; D007454:Iodides; D010165:Palladium; C004511:butenolide; D015107:4-Butyrolactone