通过芳基炔基苄醇与芳烃的形式上的[5 + 2]环化反应组装5-二苯并[,]环庚烯。
Assembly of 5-dibenzo[,]cycloheptenes by a formal [5 + 2] annulation of -aryl alkynyl benzyl alcohols with arenes.
作者信息
Zhang Zhebing, Cai Tao, Zhan Zhaohui, Xu Huiting, Yu Lemao, Luo Xiang, Li Chunmei, Gao Yuzhen, Wei Xuemei, Chen Xinzhi, Shen Runpu
机构信息
College of Chemistry and Chemical Engineering, Shaoxing University, Shaoxing, 312000, China.
Zhejiang Engineering Research Center of Fat-Soluble Vitamin, China.
出版信息
Org Biomol Chem. 2022 Sep 21;20(36):7221-7225. doi: 10.1039/d2ob01335e.
A new synthetic methodology for the synthesis of 5-dibenzo[,]cycloheptenes from -aryl alkynyl benzyl alcohols and arenes a TfO-mediated formal [5 + 2] annulation reaction has been achieved. From this transformation, structurally diverse 5-dibenzo[,]cycloheptenes were achieved in moderate to good yields. This transformation probably involves an intermolecular Friedel-Crafts-type alkylation and a subsequent intramolecular 7- cyclization in one pot, highlighting the high efficiency, regioselectivity, and step-economy of this protocol.
已实现一种由β-芳基炔丙基苄醇和芳烃合成5-二苯并[a,e]环庚烯的新合成方法——一种三氟甲磺酸根介导的形式上的[5+2]环化反应。通过这种转化，以中等至良好的产率得到了结构多样的5-二苯并[a,e]环庚烯。这种转化可能涉及一锅法中的分子间傅克型烷基化和随后的分子内7-环化，突出了该方法的高效率、区域选择性和步骤经济性。
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