Decarboxylative cyclizations and cycloadditions of palladium-polarized aza-ortho-xylylenes |
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Authors: | Chao Wang |
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Institution: | Department of Chemistry, The University of Kansas, 1251 Wescoe Hall Dr., Lawrence, KS 66045, United States |
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Abstract: | Vinyl benzoxazinones undergo decarboxylation in the presence of palladium catalysts to form palladium-polarized aza-ortho-xylylenes, which are versatile reaction intermediates. These palladium-polarized aza-ortho-xylylenes are generated under exceptionally mild conditions and undergo a plethora of different reactions depending on the reaction conditions. Specifically, they undergo dimerization reactions to produce macrocycles, cyclizations to form dihydroquinolines, cycloadditions with electrophilic p-bonds, and nucleophilic attack by amines. Thus, a wide array of structurally unique aniline derivatives can be accessed from these unique intermediates. |
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