Catalytic Methods for Aromatic C-H Amination: An Ideal Strategy for Nitrogen-Based Functional Molecules

被引:445
作者
Jiao, Jiao [1 ,2 ]
Murakami, Kei [1 ,2 ]
Itami, Kenichiro [1 ,2 ,3 ]
机构
[1] Nagoya Univ, Inst Transformat Biomol WPI ITbM, Chikusa Ku, Nagoya, Aichi 4648602, Japan
[2] Nagoya Univ, Grad Sch Sci, Chikusa Ku, Nagoya, Aichi 4648602, Japan
[3] Nagoya Univ, Itami Mol Nanocarbon Project, JST, ERATO,Chikusa Ku, Nagoya, Aichi 4648602, Japan
关键词
direct aromatic C-H transformation; amination; amidation; imidation; N BOND FORMATION; ONE-POT SYNTHESIS; METAL-FREE ROUTE; INTERMOLECULAR AMINATION; ELECTROPHILIC AMINATION; SULFONYL AZIDES; COUPLING REACTIONS; DIRECT AMIDATION; SIMPLE ARENES; ARYL AZIDES;
D O I
10.1021/acscatal.5b02417
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Transformations of aromatic compounds into the corresponding amines, amides, and imides through carbon-hydrogen (C-H) bond functionalization represent one of the most step- and atom-economical methods for the synthesis of arylamine compounds. Because arylamines are privileged structures in materials- and biology-oriented functional molecules, the development of novel and efficient synthetic methods for aromatic C-H amination has received significant attention from a wide range of research fields including materials and pharmaceuticals. This review covers recent advances in catalytic aromatic C-H amination reactions. An array of recently developed new reactions are categorized by the nature of aromatic substrates: (1) 5-membered heteroarenes, (2) arenes having a nitrogen moiety in the molecule (intramolecular C-H amination), (3) arenes having a directing group, (4) simple arenes with excess amounts, and (5) simple arenes as the limiting reagents.
引用
收藏
页码:610 / 633
页数:24
相关论文
共 339 条
[11]   Kinase Domain Mutations in Cancer: Implications for Small Molecule Drug Design Strategies [J].
Bikker, Jack A. ;
Brooijmans, Natasja ;
Wissner, Allan ;
Mansour, Tarek S. .
JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (06) :1493-1509
[12]  
Booth G., 2005, ULLMANNS ENCY IND CH
[13]   Pd-Catalyzed Aryl C-H Imidation with Arene as the Limiting Reagent [J].
Boursalian, Gregory B. ;
Ngai, Ming-Yu ;
Hojczyk, Katarzyna N. ;
Ritter, Tobias .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (36) :13278-13281
[14]   Visible light C-H amidation of heteroarenes with benzoyl azides [J].
Brachet, E. ;
Ghosh, T. ;
Ghosh, I. ;
Koenig, B. .
CHEMICAL SCIENCE, 2015, 6 (02) :987-992
[15]  
BRESLOW DS, 1968, TETRAHEDRON LETT, P5349
[16]   INTRAMOLECULAR NITRENE C-H INSERTIONS MEDIATED BY TRANSITION-METAL COMPLEXES AS NITROGEN ANALOGS OF CYTOCHROME-P-450 REACTIONS [J].
BRESLOW, R ;
GELLMAN, SH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (22) :6728-6729
[17]   TOSYLAMIDATION OF CYCLOHEXANE BY A CYTOCHROME-P-450 MODEL [J].
BRESLOW, R ;
GELLMAN, SH .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (24) :1400-1401
[18]   I2/TBHP-Catalyzed Chemoselective Amination of Indoles [J].
Cai, Zhong-Jian ;
Wang, Shun-Yi ;
Ji, Shun-Jun .
ORGANIC LETTERS, 2013, 15 (20) :5226-5229
[19]  
Catellani M, 2005, TOP ORGANOMETAL CHEM, V14, P21
[20]   Catalytic Sequential Reactions Involving Palladacycle-Directed Aryl Coupling Steps [J].
Catellani, Marta ;
Motti, Elena ;
Della Ca, Nicola .
ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (11) :1512-1522