Wang Miao, Tang Bo-Cheng, Xiang Jia-Chen, Cheng Yan, Wang Zi-Xuan, Ma Jin-Tian, Wu Yan-Dong, Wu An-Xin
Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry , Central China Normal University , Hubei , Wuhan 430079 , P. R. China.
J Org Chem. 2018 Mar 16;83(6):3409-3416. doi: 10.1021/acs.joc.8b00126. Epub 2018 Mar 1.
An efficient base-promoted C(sp)-H bond functionalization strategy for the synthesis of multisubstituted chromans from the formal [3+3] cycloaddition of benzo[ c]oxepines and electron-rich phenols has been developed. The corresponding 4 H-chromenes can be easily obtained in excellent yields by simple filtration from chromans. Preliminary mechanistic studies indicate that the C-O bond cleavage is the key step for the C(sp)-H bond functionalization and that this reaction could have occurred through tandem C-O bond cleavage/Michael addition/annulation reactions.
已开发出一种高效的碱促进的C(sp)-H键官能团化策略，用于从苯并[c]氧杂环庚三烯与富电子酚的形式[3+3]环加成反应合成多取代色满。通过从色满中简单过滤，可轻松以优异产率获得相应的4H-色烯。初步机理研究表明，C-O键断裂是C(sp)-H键官能团化的关键步骤，且该反应可能通过串联C-O键断裂/迈克尔加成/环化反应发生。
