Expeditious synthesis of 3,4-dihydroisocoumarins and phthalides using the Heck-Matsuda reaction

TETRAHEDRON LETTERS

卷:52

Article

da Penha, Eduardo T.¹  Forni, Jose Augusto¹  Biajoli, Andre F. P.¹  Correia, Carlos Roque D.¹ 

[1] Univ Estadual Campinas, Inst Quim, UNICAMP, BR-13084917 Campinas, SP, Brazil

关键词: 3-Aryl-3,4-dihydroisocoumarins;    Phthalides;    Ortho carboxybenzenediazonium salt;    Palladium;    Heck-Matsuda;   

DOI  :  10.1016/j.tetlet.2011.09.014

来源: Elsevier

【 摘 要 】

Several 3,4-dihydroisocoumarins and phthalides were synthesized by an effective Heck-Matsuda reaction involving an ortho carboxybenzenediazonium salt with a series of styrenes bearing electron donating and electron withdrawing groups, methylvinyl ketone, and methyl acrylate. The reaction was carried out in an open-flask with 1% mol of palladium acetate in aqueous ethanol at similar to 80 degrees C, giving the correspondent 3-aryl-3,4-dihydroisocoumarins and phthalides with good overall yields. The electronic nature of the group attached to the olefin is a key feature for the regioselectivity of the cyclization step. (C) 2011 Elsevier Ltd. All rights reserved.

【 授权许可】

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