Pd-Catalyzed Denitrative Intramolecular C-H Arylation

被引:45
作者
Asahara, Kitty K. [1 ]
Okita, Toshimasa [1 ]
Saito, Ami N. [1 ]
Muto, Kei [1 ]
Nakao, Yoshiaki [2 ]
Yamaguchi, Junichiro [1 ]
机构
[1] Waseda Univ, Dept Appl Chem, Shinjuku Ku, 3-4-1 Ohkubo, Tokyo 1698555, Japan
[2] Kyoto Univ, Grad Sch Engn, Dept Mat Chem, Kyoto 6158510, Japan
关键词
BOND ACTIVATION; COUPLING REACTIONS; FUNCTIONALIZATION; DECARBONYLATION; HETEROARENES; CHLORIDES;
D O I
10.1021/acs.orglett.9b01593
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A Pd-catalyzed intramolecular C-H arylation of nitroarenes has been developed. Nitroarenes bearing tethered aryl groups at the ortho-position can be readily prepared in one step from 2-halonitroarenes by a nucleophilic aromatic substitution (SNAr). Under Pd/BrettPhos catalysis, activations of the C-NO2 bond as well as the C-H bond on arenes generated the corresponding biaryl linkage in moderate to excellent yields.
引用
收藏
页码:4721 / 4724
页数:4
相关论文
共 44 条
[1]   Catalytic arylation reactions by C-H bond activation with aryl tosylates [J].
Ackermann, L ;
Althammer, A ;
Born, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (16) :2619-2622
[2]   Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Kapdi, Anant R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826
[3]   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
[4]   CuI catalyzed C-S bond formation by using nitroarenes [J].
Bahekar, Sushilkumar S. ;
Sarkate, Aniket P. ;
Wadhai, Vijay M. ;
Wakte, Pravin S. ;
Shinde, Devanand B. .
CATALYSIS COMMUNICATIONS, 2013, 41 :123-125
[5]   Transition Metal-Mediated Direct C-H Arylation of Heteroarenes Involving Aryl Radicals [J].
Bonin, Helene ;
Sauthier, Mathieu ;
Felpin, Francois-Xavier .
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (04) :645-671
[6]   Catalytic direct arylation with aryl chlorides, bromides, and iodides: Intramolecular studies leading to new intermolecular reactions [J].
Campeau, LC ;
Parisien, M ;
Jean, A ;
Fagnou, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (02) :581-590
[7]   High-yielding intramolecular direct arylation reactions with aryl chlorides [J].
Campeau, LC ;
Thansandote, P ;
Fagnou, K .
ORGANIC LETTERS, 2005, 7 (09) :1857-1860
[8]   Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality [J].
Chen, Xiao ;
Engle, Keary M. ;
Wang, Dong-Hui ;
Yu, Jin-Quan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5094-5115
[9]   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
[10]   Biaryl synthesis with arenediazonium salts: cross-coupling, CH-arylation and annulation reactions [J].
Felpin, Francois-Xavier ;
Sengupta, Saumitra .
CHEMICAL SOCIETY REVIEWS, 2019, 48 (04) :1150-1193