Pd-catalyzed arylation/aza-Michael addition cascade to C2-spiroindolines and azabicyclo[3.2.2]nonanones
Pd-catalyzed arylation/aza-Michael addition cascade to C2-spiroindolines and azabicyclo[3.2.2]nonanones
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Pd 催化的芳基化/氮杂迈克尔加成级联反应生成 C2-螺吲哚啉和氮杂双环[3.2.2]壬酮
DOI：
10.1039/d0cc04935b
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发表时间：
2020
影响因子：
4.9
通讯作者：
Wen-Bo Liu
中科院分区：
文献类型：
--
作者：
Xiao-Wen Zhang;Hui Zhang;Hu-Chong Wang;Ming-Hui Zhu;Hengjiang Cong;Wen-Bo Liu
报道了钯催化下β-取代环烯酮与2-卤代苯胺的芳基化/氮杂Michael加成级联反应。以1 mol% Pd（PPh 3）4为催化剂，β-烷基环烯酮与2-卤代苯胺发生分子间乙烯基芳基化反应，然后进行分子内氮杂Michael加成，得到C2-螺吲哚啉.该转化的官能团耐受性由18个实例检查，产率高达93%。在第二部分中，我们发展了一种α′-芳基化/氮杂Michael加成级联反应策略，以Pd（MeCN）2Cl 2·PPh 3为催化剂，合成了氮杂双环[3.2.2]壬酮。本研究提供了一种从容易获得的起始原料快速合成复杂和有用的螺环和桥环杂环化合物的方法，产率高，区域选择性高。
A palladium-catalyzed arylation/aza-Michael addition cascade reaction of β-substituted cyclic enones and 2-haloanilines has been reported. Using 1 mol% Pd(PPh3)4 as a catalyst, C2-spiroindolines are accessed via an intermolecular vinylogous arylation of β-alkyl cyclic enones and 2-haloanilines followed by an intramolecular aza-Michael addition. The functional group tolerance of this transformation is examined by 18 examples in up to 93% yield. In the second part, we developed an α′-arylation/aza-Michael addition cascade strategy to construct azabicyclo[3.2.2]nonanones catalyzed by Pd(MeCN)2Cl2·PPh3. This study provides a quick route to complex and useful spiro- and bridged-heterocycles from readily available starting materials in good yields with high regioselectivity.