C(sp(3))-H Bond Functionalization of Benzo[c]oxepines via C-O bond Cleavage: Formal [3+3] Synthesis of Multisubstituted Chromans
C(sp(3))-H Bond Functionalization of Benzo[c]oxepines via C-O bond Cleavage: Formal [3+3] Synthesis of Multisubstituted Chromans
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通过 C-O 键断裂对苯并[c]氧杂环己烷进行 C(sp(3))-H 键功能化：形式 [3 3] 多取代色满的合成
DOI：
10.1021/acs.joc.8b00126
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发表时间：
2018
影响因子：
3.6
通讯作者：
Wu An-Xin
中科院分区：
文献类型：
--
作者：
Wang Miao;Tang Bo-Cheng;Xiang Jia-Chen;Cheng Yan;Wang Zi-Xuan;Ma Jin-Tian;Wu Yan-Dong;Wu An-Xin
提出了一种有效的碱促进的C（sp3）-H键官能化策略，通过苯并[c]氧杂卓与富电子苯酚的[3+3]环加成反应合成多取代色满.相应的4 H-色烯可以通过简单的过滤从色满容易地以优异的产率获得。初步的机理研究表明，C-O键断裂是C（sp3）-H键功能化的关键步骤，该反应可能是通过C-O键断裂/Michael加成/成环的串联反应进行的。
An efficient base-promoted C(sp3)–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 4H-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(sp3)–H bond functionalization and that this reaction could have occurred through tandem C–O bond cleavage/Michael addition/annulation reactions.