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The same research group developed two different protocols for the preparation of 2-substituted-3- allylbenzofurans from o-alkynylphenols and allyl carbonates under palladium catalysis ¡£ The stepwise method (method A) was based on the preparation of stereo- and regioisomeric mixtures of O-allyl derivatives and their subsequent cyclization to benzofurans, being the method of choice when steric differences between the two allylic termini are small. The one-pot protocol (method B), omitting isolation of the O-allyl derivatives, was employed when the reaction proceeds through ¨¨3-allylpalladium complexes and also when the two allylic termini are markedly different from a steric point of view. Concerning the reaction mechanism, the cyclization of the O-allyl derivatives was suggested to proceed through the palladium-promoted ionization of the allylic C-O bond and displacement of one ligand to the palladium by the carbon-carbon triple bond, intramolecular nucleophilic attack of the oxygen atom across the activated carbon-carbon triple bond, and reductive elimination ¡£ |
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answerball(½ð±Ò+1, ·ÒëEPI+1): 2011-02-21 16:05:23
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The stepwise method (method A) was based on the preparation of stereo- and regioisomeric mixtures of O-allyl derivatives and their subsequent cyclization to benzofurans, being the method of choice when steric differences between the two allylic termini are small. ·Ö²¼·´Ó¦£¨·½·¨A£©ÊÇ»ùÓÚO-Ï©±û»ùÈ¡´úÎïÒÔ¼°½ÓÏÂÀ´µÄ»·»¯Ðγɱ½²¢ß»à«Á¢ÌåÑ¡ÔñÐÔºÍÇøÓòÑ¡ÔñÐÔ»ìºÏÎï¡£¸Ã·½·¨ÔÚµ±Á½ÖÖÏ©±û»ùÄ¿±ê·Ö×ÓµÄÁ¢Ìå²î±ð²»´óʱʹÓã¡ |
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The same research group developed two different protocols for the preparation of 2-substituted-3-allylbenzofurans from o-alkynylphenols and allyl carbonates under palladium catalysis. ͬһ¸öÑо¿Ð¡×鿪·¢ÁËÁ½ÖÖ²»Í¬µÄ·½·¨£¬¶¼ÊÇÔÚîÙ´ß»¯Ìõ¼þÏ£¬ÓÉÁÚ±½»ù±½·ÓÍé»ùºÍ̼ËáÑκϳÉ2-È¡´ú-3Ï©±û»ù±½²¢ß»à«¡£ |
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