Copper-Catalyzed Hydrogen Atom Transfer and Aryl Migration Strategy for the Arylalkylation of Activated Alkenes

被引:15
作者
Chen, Xi [1 ]
Wang, Qiang [2 ,3 ]
Zhang, Zhe [1 ]
Niu, Zhi-Jie [1 ]
Shi, Wei-Yu [1 ]
Gong, Xiao-Ping [1 ]
Jiao, Rui-Qiang [1 ]
Gao, Ming-Hui [1 ]
Liu, Xue-Yuan [1 ]
Liang, Yong-Min [1 ]
机构
[1] Lanzhou Univ, Sch Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
[2] Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Peoples R China
[3] Southern Univ Sci & Technol, Dept Chem, Guangdong Prov Key Lab Catalysis, Shenzhen 518055, Peoples R China
基金
中国国家自然科学基金;
关键词
QUATERNARY CARBON CENTERS; ENANTIOSELECTIVE CONSTRUCTION; MIGRATION/DESULFONYLATION; STEREOCENTERS; FLUORINATION;
D O I
10.1021/acs.orglett.2c01427
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, we describe the copper-catalyzed arylalkylation of activated alkenes via hydrogen-atom transfer and aryl migration strategy. The reaction was carried out through a radical-mediated continuous migration pathway using N-fluorosulfonamides as the alkyl source. The primary, secondary, and tertiary alkyl radicals formed by intramolecular hydrogenatom transfer proceeded smoothly. This methodology is an efficient approach for the synthesis of various amide derivatives possessing a quaternary carbon center with good yields and high regioselectivity.
引用
收藏
页码:4338 / 4343
页数:6
相关论文
共 61 条
[1]   Radical Smiles Rearrangement: An Update [J].
Allart-Simon, Ingrid ;
Gerard, Stephane ;
Sapi, Janos .
MOLECULES, 2016, 21 (07)
[2]   Copper-Catalyzed N-F Bond Activation for Uniform Intramolecular C-H Amination Yielding Pyrrolidines and Piperidines [J].
Bafaluy, Daniel ;
Maria Munoz-Molina, Jose ;
Funes-Ardoiz, Ignacio ;
Herold, Sebastian ;
de Aguirre, Adiran J. ;
Zhang, Hongwei ;
Maseras, Feliu ;
Belderrain, Tomas R. ;
Perez, Pedro J. ;
Muniz, Kilian .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (26) :8912-8916
[3]   Organocatalytic Formation of Quaternary Stereocenters [J].
Bella, Marco ;
Gasperi, Tecla .
SYNTHESIS-STUTTGART, 2009, (10) :1583-1614
[4]   Molecular Oxygen Mediated Radical Dicarbofunctionalization of Olefin with Aldehyde [J].
Biswas, Promita ;
Guin, Joyram .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (10) :5629-5638
[5]   Copper-Catalyzed N-Directed Distal C(sp3)-H Sulfonylation and Thiolation with Sulfinate Salts [J].
Chen, Guang-Le ;
He, Shi-Hui ;
Cheng, Liang ;
Liu, Feng .
ORGANIC LETTERS, 2021, 23 (21) :8338-8342
[6]   Construction of quaternary stereocenters: New perspectives through enantioselective Michael reactions [J].
Christoffers, J ;
Baro, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (15) :1688-1690
[7]  
Christoffers J, 2001, ANGEW CHEM INT EDIT, V40, P4591, DOI 10.1002/1521-3773(20011217)40:24<4591::AID-ANIE4591>3.0.CO
[8]  
2-V
[9]  
Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P388, DOI 10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO
[10]  
2-V