Polycyclization Enabled by Relay Catalysis: One-Pot Manganese-Catalyzed C-H Allylation and Silver-Catalyzed Povarov Reaction

被引:57
作者
Chen, Shi-Yong [1 ]
Li, Qingjiang [1 ,2 ]
Liu, Xu-Ge [1 ]
Wu, Jia-Qiang [1 ]
Zhang, Shang-Shi [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, Peoples R China
基金
中国国家自然科学基金;
关键词
C-H activation; cycloaddition; manganese; relay catalysis; silver; ELECTRON-DEFICIENT ARENES; CARBON-HYDROGEN BONDS; N-TYPE REACTIONS; ROOM-TEMPERATURE; ALLYLIC ALCOHOLS; NATURAL-PRODUCTS; ACTIVATION; FUNCTIONALIZATION; ALKYLATION; BENZAMIDES;
D O I
10.1002/cssc.201700452
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In this study, a MnI/AgI-based relay catalysis process is described for the one-pot synthesis of polycyclic products by a formal [3+2] and [4+2] cycloaddition reaction cascade. A manganese(I) complex catalyzed the first example of directed C-H allylation with allenes, setting the stage for an in situ Povarov cyclization catalyzed by silver(I). The reaction proceeds with high bond-forming efficiency (three C-C bonds), broad substrate scope, high regio- and stereoselectivity, and 100% atom economy.
引用
收藏
页码:2360 / 2364
页数:5
相关论文
共 106 条
[1]   Robust Ruthenium(II)-Catalyzed C-H Arylations: Carboxylate Assistance for the Efficient Synthesis of Angiotensin-II-Receptor Blockers [J].
Ackermann, Lutz .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2015, 19 (01) :260-269
[2]   Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].
Ackermann, Lutz .
CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345
[3]   Nickel-Catalyzed Direct Alkylation of C-H Bonds in Benzamides and Acrylamides with Functionalized Alkyl Halides via Bidentate-Chelation Assistance [J].
Aihara, Yoshinori ;
Chatani, Naoto .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (14) :5308-5311
[4]  
Anastas P., 1998, GREEN CHEM THEORY PR
[5]  
[Anonymous], 2013, ANGEW CHEM, V125, P5495
[6]  
[Anonymous], 2013, ANGEW CHEM, V125, P11942
[7]  
[Anonymous], 2016, ANGEW CHEM, V128, P7878
[8]  
[Anonymous], 2012, ANGEW CHEM, V124, P10382
[9]  
[Anonymous], 2011, ANGEW CHEM, V123, P6040
[10]  
[Anonymous], 2015, ANGEW CHEM, V127, P13863