Cobalt-Catalyzed Selective Synthesis of Isoquinolines Using Picolinamide as a Traceless Directing Group

被引:99
作者
Kuai, Changsheng [1 ]
Wang, Lianhui [1 ]
Li, Bobin [1 ]
Yang, Zhenhui [1 ]
Cui, Xiuling [1 ]
机构
[1] Huaqiao Univ, Sch Biomed Sci, Key Lab Xiamen Marine & Gene Drugs, Engn Res Ctr Mol Med,Minist Educ,Key Lab Fujian M, Xiamen 361021, Peoples R China
关键词
C-H ACTIVATION; C(SP(3))-H BOND ACTIVATION; HETEROCYCLE SYNTHESIS; IRIDIUM COMPLEXES; CARBOXYLIC-ACIDS; ELECTROCHEMICAL PROPERTIES; BETA-PHENYLETHYLAMINES; FUNCTIONAL MOLECULES; ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS;
D O I
10.1021/acs.orglett.7b00702
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Picolinamide has first been employed as a traceless directing group for the cobalt-catalyzed oxidative annulation of benzylamides with alkynes to synthesize isoquinolines through C-H/N-H bonds activation. Oxygen is used as a terminal oxidant. This protocol exhibits good functional group tolerance and excellent regioselectivity. Both terminal and internal alkynes can be efficiently applied to this catalytic system as substrates.
引用
收藏
页码:2102 / 2105
页数:4
相关论文
共 74 条
[1]   Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations [J].
Ackermann, Lutz .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) :281-295
[2]   Cobalt(III) catalyzed C-8 selective C-H and C-O coupling of quinoline N-oxide with internal alkynes via C-H activation and oxygen atom transfer [J].
Barsu, Nagaraju ;
Sen, Malay ;
Premkumar, J. Richard ;
Sundararaju, Basker .
CHEMICAL COMMUNICATIONS, 2016, 52 (07) :1338-1341
[3]   β-Phenylethylamines and the isoquinoline alkaloids [J].
Bentley, Kenneth W. .
NATURAL PRODUCT REPORTS, 2006, 23 (03) :444-463
[4]   BETA-PHENYLETHYLAMINES AND THE ISOQUINOLINE ALKALOIDS [J].
BENTLEY, KW .
NATURAL PRODUCT REPORTS, 1992, 9 (04) :365-391
[5]   PyDipSi: A General and Easily Modifiable/Traceless Si-Tethered Directing Group for C-H Acyloxylation of Arenes [J].
Chernyak, Natalia ;
Dudnik, Alexander S. ;
Huang, Chunhui ;
Gevorgyan, Vladimir .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (24) :8270-+
[6]   Asymmetric synthesis of isoquinoline alkaloids [J].
Chrzanowska, M ;
Rozwadowska, MD .
CHEMICAL REVIEWS, 2004, 104 (07) :3341-3370
[7]   Carboxylic Acids as Traceless Directing Groups for Formal meta-Selective Direct Arylation [J].
Cornella, Josep ;
Righi, Marika ;
Larrosa, Igor .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (40) :9429-9432
[8]   Branch Selective Mural-type Alkene Hydroarylation Reactions [J].
Crisenza, Giacomo E. M. ;
Bower, John F. .
CHEMISTRY LETTERS, 2016, 45 (01) :2-9
[9]   Recent Advances in C-H Functionalization [J].
Davies, Huw M. L. ;
Morton, Daniel .
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (02) :343-350
[10]   Weakly Coordinating Directing Groups for Ruthenium(II)-Catalyzed C-H Activation [J].
De Sarkar, Suman ;
Liu, Weiping ;
Kozhushkov, Sergei I. ;
Ackermann, Lutz .
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (07) :1461-1479