Nickel-Catalyzed Aromatic C-H Functionalization

被引:73
作者
Yamaguchi, Junichiro [1 ]
Muto, Kei [1 ]
Itami, Kenichiro [2 ,3 ,4 ]
机构
[1] Waseda Univ, Dept Appl Chem, Tokyo 1698555, Japan
[2] Nagoya Univ, Inst Transformat Biomol WPI ITbM, Chikusa Ku, Nagoya, Aichi 4648602, Japan
[3] Nagoya Univ, Grad Sch Sci, Chikusa Ku, Nagoya, Aichi 4648602, Japan
[4] Nagoya Univ, JST ERATO, Itami Mol Nanocarbon Project, Chikusa Ku, Nagoya, Aichi 4648602, Japan
关键词
C-H functionalization; C-H activation; Nickel; Heteroarenes; Arenes; Catalyst; UNACTIVATED C(SP(3))-H BONDS; BIDENTATE-CHELATION ASSISTANCE; DIRECT ALKYLATION; ALIPHATIC AMIDES; DIRECT ARYLATION; ACID CATALYSIS; THIOPEPTIDE ANTIBIOTICS; SELECTIVE ALKENYLATION; SYNERGISTIC CATALYSIS; ORGANOZINC REAGENTS;
D O I
10.1007/s41061-016-0053-z
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Catalytic C-H functionalization using transition metals has received significant interest from organic chemists because it provides a new strategy to construct carbon-carbon bonds and carbon-heteroatom bonds in highly functionalized, complex molecules without pre-functionalization. Recently, inexpensive catalysts based on transition metals such as copper, iron, cobalt, and nickel have seen more use in the laboratory. This review describes recent progress in nickelcatalyzed aromatic C-H functionalization reactions classified by reaction types and reaction partners. Furthermore, some reaction mechanisms are described and cutting-edge syntheses of natural products and pharmaceuticals using nickel-catalyzed aromatic C-H functionalization are presented.
引用
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页数:33
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共 115 条
[1]   Nickel-Catalyzed Reaction of C-H Bonds in Amides with I2: ortho-Iodination via the Cleavage of C(sp2)-H Bonds and Oxidative Cyclization to β-Lactams via the Cleavage of C(sp3)-H Bonds [J].
Aihara, Yoshinori ;
Chatani, Naoto .
ACS CATALYSIS, 2016, 6 (07) :4323-4329
[2]   The Nickel(II)-Catalyzed Direct Benzylation, Allylation, Alkylation, and Methylation of C-H Bonds in Aromatic Amides Containing an 8-Aminoquinoline Moiety as the Directing Group [J].
Aihara, Yoshinori ;
Wuelbern, Jendrik ;
Chatani, Naoto .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2015, 88 (03) :438-446
[3]   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
[4]   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
[5]   Synthesis of Triarylpyridines in Thiopeptide Antibiotics by Using a C-H Arylation/Ring-Transformation Strategy [J].
Amaike, Kazuma ;
Itami, Kenichiro ;
Yamaguchi, Junichiro .
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (13) :4384-4388
[6]   Decarbonylative C-H Coupling of Azoles and Aryl Esters: Unprecedented Nickel Catalysis and Application to the Synthesis of Muscoride A [J].
Amaike, Kazuma ;
Muto, Kei ;
Yamaguchi, Junichiro ;
Itami, Kenichiro .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) :13573-13576
[7]   Linear-Selective Hydroarylation of Unactivated Terminal and Internal Olefins with Trifluoromethyl-Substituted Arenes [J].
Bair, Joseph S. ;
Schramm, York ;
Sergeev, Alexey G. ;
Clot, Eric ;
Eisenstein, Odile ;
Hartwig, John F. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (38) :13098-13101
[8]   Carboxylate Assisted Ni-Catalyzed CH Bond Allylation of Benzamides [J].
Barsu, Nagaraju ;
Kalsi, Deepti ;
Sundararaju, Basker .
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (26) :9364-9368
[9]   Recent advances in nickel-catalyzed C-H bond functionalized reactions [J].
Cai, Xiao-hua ;
Xie, Bing .
ARKIVOC, 2015, :184-211
[10]   Nickel-Catalyzed Biaryl Coupling of Heteroarenes and Aryl Halides/Triflates [J].
Canivet, Jerome ;
Yamaguchi, Junichiro ;
Ban, Ikuya ;
Itami, Kenichiro .
ORGANIC LETTERS, 2009, 11 (08) :1733-1736