Cooperative Lewis Acid/Cp*CoIII Catalyzed C-H Bond Activation for the Synthesis of Isoquinolin-3-ones

被引：166

作者：

Kim, Ju Hyun ^{[1
]}

Gressies, Steffen ^{[1
]}

Glorius, Frank ^{[1
]}

机构：

[1] Univ Munster, Inst Organ Chem, Corrensstr 40, D-48149 Munster, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 18期

关键词：

carbenes; C-H activation; cobalt; cooperative catalysis; isoquinolinones; ONE-POT SYNTHESIS; SELECTIVE ALKENYLATION; OXIDATIVE ANNULATION; AROMATIC KETIMINES; ARYLZINC REAGENTS; ALKYNES; IMINES; ROUTE; DERIVATIVES; AMIDATION;

D O I：

10.1002/anie.201601003

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A facile route toward the synthesis of isoquinolin-3-ones through a cooperative B(C6F5)(3)- and Cp*Co-III-catalyzed C-H bond activation of imines with diazo compounds is presented. The inclusion of a catalytic amount of B(C6F5)(3) results in a highly efficient reaction, thus enabling unstable NH imines to serve as substrates.

引用

页码：5577 / 5581

页数：5

共 97 条

[21] A new route to dual fluorescence: Spectroscopic properties of the valence tautomers of a 3-(2H)-isoquinolinone derivative
Craig, Ian M.
Duong, Hieu M.
Wudl, Fred
Schwartz, Benjamin J.
[J]. CHEMICAL PHYSICS LETTERS, 2009, 477 (4-6) : 319 - 324
[22] Deng Y., 2014, ANGEW CHEM, V126, P6810
[23] Ligand-Enabled Triple C-H Activation Reactions: One-Pot Synthesis of Diverse 4-Aryl-2-quinolinones from Propionamides
Deng, Youqian
Gong, Wei
He, Jian
Yu, Jin-Quan
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (26) : 6692 - 6695
[24] TOTAL SYNTHESIS OF AMPHIMEDINE
ECHAVARREN, AM
STILLE, JK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (12) : 4051 - 4053
[25] C-H Activation/Functionalization Catalyzed by Simple, Well-Defined Low-Valent Cobalt Complexes
Fallon, Brendan J.
Derat, Etienne
Amatore, Muriel
Aubert, Corinne
Chemla, Fabrice
Ferreira, Franck
Perez-Luna, Alejandro
Petit, Marc
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (07) : 2448 - 2451
[26] Selective Synthesis of Isoquinolin-3-one Derivatives Combining Pd-Catalysed Aromatic Alkylation/Vinylation with Addition Reactions: The Beneficial Effect of Water
Ferraccioli, Raffaella
Forni, Alessandra
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (19) : 3161 - 3166
[27] Octahedral group 4 metal complexes that contain amine, amido, and aminopyridinato ligands: Synthesis, structure, and application in alpha-olefin oligo- and polymerization
Fuhrmann, H
Brenner, S
Arndt, P
Kempe, R
[J]. INORGANIC CHEMISTRY, 1996, 35 (23) : 6742 - 6745
[28] Advancements in the Synthesis and Applications of Cationic N-Heterocycles through Transition Metal-Catalyzed C-H Activation
Gandeepan, Parthasarathy
Cheng, Chien-Hong
[J]. CHEMISTRY-AN ASIAN JOURNAL, 2016, 11 (04) : 448 - 460
[29] Low-Valent Cobalt Catalysis: New Opportunities for C-H Functionalization
Gao, Ke
Yoshikai, Naohiko
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (04) : 1208 - 1219
[30] Cobalt-catalyzed arylation of aldimines via directed C-H bond functionalization: addition of 2-arylpyridines and self-coupling of aromatic aldimines
Gao, Ke
Yoshikai, Naohiko
[J]. CHEMICAL COMMUNICATIONS, 2012, 48 (36) : 4305 - 4307

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