Manganese(I)-Catalyzed Regio- and Stereoselective 1,2-Diheteroarylation of Allenes: Combination of C-H Activation and Smiles Rearrangement

被引:118
作者
Chen, Shi-Yong [1 ]
Han, Xiang-Lei [1 ]
Wu, Jia-Qiang [1 ]
Li, Qingjiang [1 ,2 ]
Chen, Yunyun [1 ]
Wang, Honggen [1 ]
机构
[1] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangzhou 510006, Guangdong, Peoples R China
[2] Peking Univ, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
基金
中国国家自然科学基金;
关键词
allenes; C-H activation; heteroarylation; manganese; migration; CARBON-HYDROGEN BONDS; QUINOLINE N-OXIDES; INTERMOLECULAR ANNULATION; CATALYZED CYCLIZATION; ROOM-TEMPERATURE; DIRECTING GROUP; ATOM TRANSFER; MANGANESE; ALKYNES; ALLYLATION;
D O I
10.1002/anie.201704952
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Heteroarenes are important structural motif in functional molecules. A MnI-catalyzed 1,2-diheteroarylation of allenes via a C-H activation/Smiles rearrangement cascade is presented. The reaction occurred under additive-free or even solvent-free conditions, which allowed the creation of two C-C and one C-N bonds in a single operation. A series of structurally diverse bicyclic or tricyclic compounds bearing an exocyclic double bond were constructed in good to excellent efficiency. The decarboxylative ring-opening of the products led to the facile synthesis of vicinal biheteroaryls. Synthetic applications were demonstrated and preliminary mechanistic studies were conducted.
引用
收藏
页码:9939 / 9943
页数:5
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