Ni(II)-Catalyzed Oxidative Coupling between C(sp2)-H in Benzamides and C(sp3)-H in Toluene Derivatives

被引:222
作者
Aihara, Yoshinori [1 ]
Tobisu, Mamoru [1 ]
Fukumoto, Yoshiya [1 ]
Chatani, Naoto [1 ]
机构
[1] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
关键词
CATALYZED ORTHO-ARYLATION; H BOND ACTIVATION; C-C; PERFLUOROALKYL IODIDES; ALKYL-HALIDES; SIMPLE ARENES; FLUOROALKYLATION; FUNCTIONALIZATION;
D O I
10.1021/ja5095342
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Oxidative coupling between C((sp2)))-H bonds and C((sp3)))-H bonds is achieved by the Ni(II)-catalyzed reaction of benzamides containing an 8-aminoquinoline moiety as the directing group with toluene derivatives in the presence of heptafluoroisopropyl iodide as the oxidant. The method has a broad scope and shows high functional group compatibility. Toluene derivatives can be used as the coupling partner in an unreactive solvent.
引用
收藏
页码:15509 / 15512
页数:4
相关论文
共 49 条
[1]   Nickel-Catalyzed Direct Arylation of C(sp3)-H Bonds in Aliphatic Amides via Bidentate-Chelation Assistance [J].
Aihara, Yoshinori ;
Chatani, Naoto .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (03) :898-901
[2]   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
[3]   Mechanism and Selectivity in Nickel-Catalyzed Cross-Electrophile Coupling of Aryl Halides with Alkyl Halides [J].
Biswas, Soumik ;
Weix, Daniel J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (43) :16192-16197
[4]   Reactions of perfluoroalkyl iodides with M(C5H5)(CO)(PMe3) [M = Rh, ir];: Evidence for direct fluoroalkylation at a CO ligand [J].
Bourgeois, CJ ;
Hughes, RP ;
Husebo, TL ;
Smith, JM ;
Guzei, IM ;
Liable-Sands, LM ;
Zakharov, LN ;
Rheingold, AL .
ORGANOMETALLICS, 2005, 24 (26) :6431-6439
[6]   Twofold C-H functionalization:: Palladium-catalyzed ortho arylation of anilides [J].
Brasche, Gordon ;
Garcia-Fortanet, Jorge ;
Buchwald, Stephen L. .
ORGANIC LETTERS, 2008, 10 (11) :2207-2210
[7]   C-H Activation: A Complementary Tool in the Total Synthesis of Complex Natural Products [J].
Chen, David Y. -K. ;
Youn, So Won .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (31) :9452-9474
[8]   Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation [J].
Colby, Denise A. ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
CHEMICAL REVIEWS, 2010, 110 (02) :624-655
[9]   Catalytic Enantioselective Cyclization/Cross-Coupling with Alkyl Electrophiles [J].
Cong, Huan ;
Fu, Gregory C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (10) :3788-3791
[10]   Palladium- and Copper-Catalyzed Arylation of Carbon-Hydrogen Bonds [J].
Daugulis, Olafs ;
Do, Hien-Quang ;
Shabashov, Dmitry .
ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (08) :1074-1086