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

[61] Selective C-4 Alkylation of Pyridine by Nickel/Lewis Acid Catalysis
Nakao, Yoshiaki
Yamada, Yuuya
Kashihara, Natsuko
Hiyama, Tamejiro
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (39) : 13666 - 13668
[62] Park J., 2015, ANGEW CHEM, V127, P14309, DOI DOI 10.1002/ANGE.201505820
[63] Comparative Catalytic Activity of Group 9 [Cp*MIII] Complexes: Cobalt-Catalyzed C-H Amidation of Arenes with Dioxazolones as Amidating Reagents
Park, Juhyeon
Chang, Sukbok
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (47) : 14103 - 14107
[64] Cobalt-Catalyzed Oxidative Annulation of Nitrogen-Containing Arenes with Alkynes: An Atom-Economical Route to Heterocyclic Quaternary Ammonium Salts
Prakash, Sekar
Muralirajan, Krishnamoorthy
Cheng, Chien-Hong
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (05) : 1844 - 1848
[65] Cobalt(III)-Catalyzed Dehydrative [4+2] Annulation of Oxime with Alkyne by CH and NOH Activation
Sen, Malay
Kalsi, Deepti
Sundararaju, Basker
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (44) : 15529 - 15533
[66] Shamma M., 1978, ISOQUINOLINONE ALKAL
[67] Regioselective synthesis of multisubstituted isoquinolones and pyridones via Rh(III)-catalyzed annulation reactions
Shi, Liangliang
Yu, Ke
Wang, Baiquan
[J]. CHEMICAL COMMUNICATIONS, 2015, 51 (97) : 17277 - 17280
[68] Manganese catalyzed C-H functionalization of indoles with alkynes to synthesize bis/trisubstituted indolylalkenes and carbazoles: the acid is the key to control selectivity
Shi, Lijun
Zhong, Xiang
She, Houde
Lei, Ziqiang
Li, Fuwei
[J]. CHEMICAL COMMUNICATIONS, 2015, 51 (33) : 7136 - 7139
[69] Rh(III)-Catalyzed Synthesis of Multisubstituted Isoquinoline and Pyridine N-Oxides from Oximes and Diazo Compounds
Shi, Zhuangzhi
Koester, Dennis C.
Boultadakis-Arapinis, Melissa
Glorius, Frank
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (33) : 12204 - 12207
[70] Manganese- and Borane-Mediated Synthesis of Isobenzofuranones from Aromatic Esters and Oxiranes via C-H Bond Activation
Sueki, Shunsuke
Wang, Zijia
Kuninobu, Yoichiro
[J]. ORGANIC LETTERS, 2016, 18 (02) : 304 - 307

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