Palladium-Catalyzed Asymmetric C-H Activation for the Synthesis of Planar Chiral Ferrocene Sulfonamides

被引:0
作者
Zhang, Chaowei [1 ]
Xu, Bingbin [1 ]
Liu, Wenlong [1 ]
Zhao, Jing [1 ]
Duan, Weiliang [1 ,2 ]
机构
[1] Yangzhou Univ, Coll Chem & Chem Engn, Yangzhou 225002, Jiangsu, Peoples R China
[2] Inner Mongolia Univ, Coll Chem & Chem Engn, Hohhot 010000, Peoples R China
基金
中国国家自然科学基金;
关键词
palladium catalysis; plane chirality; ferrocene; sulfonamide; C-H bond activation; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE SYNTHESES; ORTHO-LITHIATION; SULFANILAMIDE; SILYLATION; ARYLATION; LIGANDS; REDOX; ENTRY;
D O I
10.6023/cjoc202404002
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Pd-catalyzed asymmetric synthesis of planar chiral ferrocenes by enantioselective intramolecular C-H arylation of N-(2-bromoaryl)-N-alkylferrocenesulfonamide were efficiently achieved in good enantioselectivities (up to 90% ee) and high yields.
引用
收藏
页码:707 / 716
页数:10
相关论文
共 65 条
[31]   Synthesis of planar chiral isoquinolinone-fused ferrocenes through palladium-catalyzed C-H functionalization reaction [J].
Liu, Lantao ;
Liu, Huihui ;
Zuo, Zhenzhen ;
Zhang, An-An ;
Li, Zhongyi ;
Meng, Tuanjie ;
Wu, Wei ;
Hua, Yuanzhao ;
Mao, Guoliang .
CHINESE CHEMICAL LETTERS, 2021, 32 (01) :239-242
[32]   Asymmetric Synthesis of Planar Chiral Ferrocenes by Enantioselective Intramolecular C-H Arylation of N-(2-Haloaryl)ferrocenecarboxamides [J].
Liu, Lantao ;
Zhang, An-An ;
Zhao, Rui-Juan ;
Li, Feng ;
Meng, Tuan-Jie ;
Ishida, Naoki ;
Murakami, Masahiro ;
Zhao, Wen-Xian .
ORGANIC LETTERS, 2014, 16 (20) :5336-5338
[33]   Palladium-catalyzed intramolecular Cp-H bond functionalization/arylation: an enantioselective approach to planar chiral quinilinoferrocenes [J].
Ma, Xinna ;
Gu, Zhenhua .
RSC ADVANCES, 2014, 4 (68) :36241-36244
[34]   STEREOSELECTIVE SYNTHESES .5. CORRELATION OF CENTRAL AND PLANAR CHIRALITY IN FERROCENE DERIVATIVES [J].
MARQUARDING, D ;
KLUSACEK, H ;
GOKEL, G ;
HOFFMANN, P ;
UGI, I .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (18) :5389-+
[35]  
Marshall EK Jr, 1937, J PHARMACOL EXP THER, V61, P196
[36]   Aminoferrocene-Based Prodrugs and Their Effects on Human Normal and Cancer Cells as Well as Bacterial Cells [J].
Marzenell, Paul ;
Hagen, Helen ;
Sellner, Leopold ;
Zenz, Thorsten ;
Grinyte, Ruta ;
Pavlov, Valeri ;
Daum, Steffen ;
Mokhir, Andriy .
JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (17) :6935-6944
[37]   Rhodium-Catalyzed Synthesis of Benzosilolometallocenes via the Dehydrogenative Silylation of C(sp2)-H Bonds [J].
Murai, Masahito ;
Matsumoto, Koji ;
Takeuchi, Yutaro ;
Takai, Kazuhiko .
ORGANIC LETTERS, 2015, 17 (12) :3102-3105
[38]   Catalytic Enantioselective Transformations Involving C-H Bond Cleavage by Transition-Metal Complexes [J].
Newton, Christopher G. ;
Wang, Shou-Guo ;
Oliveira, Caio C. ;
Cramer, Nicolai .
CHEMICAL REVIEWS, 2017, 117 (13) :8908-8976
[39]   Enantioselective ortho-lithiation of substituted ferrocenes [J].
Nishibayashi, Y ;
Arikawa, Y ;
Ohe, K ;
Uemura, S .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (03) :1172-1174
[40]   Kinetic Resolution of Allyl Fluorides by Enantioselective Allylic Trifluoromethylation Based on Silicon-Assisted C-F Bond Cleavage [J].
Nishimine, Takayuki ;
Fukushi, Kazunobu ;
Shibata, Naoyuki ;
Taira, Hiromi ;
Tokunaga, Etsuko ;
Yamano, Akihito ;
Shiro, Motoo ;
Shibata, Norio .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (02) :517-520