Nickel-Catalyzed Deoxygenative Deuteration of Aryl Sulfamates

被引:19
作者
Kuriyama, Masami [1 ]
Kujirada, Shota [1 ]
Tsukuda, Kotaro [1 ]
Onomura, Osamu [1 ]
机构
[1] Nagasaki Univ, Grad Sch Biomed Sci, 1-14 Bunkyo Machi, Nagasaki 8528521, Japan
关键词
Arenes; Deoxygenation; Deuteration; Nickel; Sulfamates; CROSS-COUPLING REACTIONS; ARENE H/D EXCHANGE; H BOND ACTIVATION; SELECTIVE DEUTERATION; PHENOL DERIVATIVES; ROOM-TEMPERATURE; DECARBOXYLATIVE DEUTERATION; HETEROARYL MESYLATES; GRIGNARD-REAGENTS; CARBOXYLIC-ACIDS;
D O I
10.1002/adsc.201601105
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The nickel-catalyzed deoxygenative deuteration of aryl/heteroaryl sulfamates has been developed, and the effective incorporation of deuterium into a variety of aromatic compounds was achieved with sufficient catalytic efficiency and high deuteration degree. This process tolerated reducible functional moieties and heterocyclic structures. Additionally, a double introduction of deuterium also successfully gave a desired product with a high yield and deuterium content.
引用
收藏
页码:1043 / 1048
页数:6
相关论文
共 98 条
[51]   Nickel Catalyzed Cross-Coupling of Aryl C-O Based Electrophiles with Aryl Neopentylglycolboronates [J].
Leowanawat, Pawaret ;
Zhang, Na ;
Percec, Virgil .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (02) :1018-1025
[52]   Ni(COD)2/PCy3 Catalyzed Cross-Coupling of Aryl and Heteroaryl Neopentylglycolboronates with Aryl and Heteroaryl Mesylates and Sulfamates in THF at Room Temperature [J].
Leowanawat, Pawaret ;
Zhang, Na ;
Resmerita, Ana-Maria ;
Rosen, Brad M. ;
Percec, Virgil .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (24) :9946-9955
[53]  
Liu X., 2016, ANGEW CHEM, V128, P6918
[54]   Lewis Acid Assisted Nickel-Catalyzed Cross-Coupling of Aryl Methyl Ethers by C-O Bond-Cleaving Alkylation: Prevention of Undesired -Hydride Elimination [J].
Liu, Xiangqian ;
Hsiao, Chien-Chi ;
Kalvet, Indrek ;
Leiendecker, Matthias ;
Guo, Lin ;
Schoenebeck, Franziska ;
Rueping, Magnus .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (20) :6093-6098
[55]   Nickel-Catalyzed Cross-Coupling of Aryl Bromides with Tertiary Grignard Reagents Utilizing Donor-Functionalized N-Heterocyclic Carbenes (NHCs) [J].
Lohre, Claudia ;
Droege, Thomas ;
Wang, Congyang ;
Glorius, Frank .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (22) :6052-6055
[56]  
Ma S., 2014, Angew. Chem. Int. Ed, V126, P753
[57]   Palladium-Catalyzed ortho-Selective C-H Deuteration of Arenes: Evidence for Superior Reactivity of Weakly Coordinated Palladacycles [J].
Ma, Sandy ;
Villa, Giorgio ;
Thuy-Boun, Peter S. ;
Homs, Anna ;
Yu, Jin-Quan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (03) :734-737
[58]   Large-Scale Applications of Transition Metal-Catalyzed Couplings for the Synthesis of Pharmaceuticals [J].
Magano, Javier ;
Dunetz, Joshua R. .
CHEMICAL REVIEWS, 2011, 111 (03) :2177-2250
[59]   Palladium-catalyzed decarboxylation and decarbonylation under hydrothermal conditions: Decarboxylative deuteration [J].
Matsubara, S ;
Yokota, Y ;
Oshima, K .
ORGANIC LETTERS, 2004, 6 (12) :2071-2073
[60]   Synopsis of Some Recent Tactical Application of Bioisosteres in Drug Design [J].
Meanwell, Nicholas A. .
JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (08) :2529-2591