A mechanistic study of the Lewis base-directed cycloaddition of 2-pyrones and alkynylboranes.
作者： Damien F. P. Crépin , Joseph P. A. Harrity , Julong Jiang , Anthony J. H. M. Meijer , Anne-Chloé M. A. Nassoy
DOI: 10.1021/JA501805R
关键词:
摘要: Significant rate enhancements in the Diels–Alder reaction of alkynes and 2-pyrones bearing a Lewis basic group are observed when combination alkynyltrifluoroborates BF3·OEt2 is used. This process generates functionalized aromatic compounds with complete regiocontrol. The enhancement was studied by density functional theory methods appears to originate from coordination diene substrate mixture alkynylborane intermediates, followed acid-mediated product equilibration step. Evidence for this mechanism presented, as enhanced promotion cycloaddition via use alternative acid promoters.
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