Recent advances using [Cp*Co(CO)I2] catalysts as a powerful tool for C-H functionalisation

被引:112
作者
Chirila, Paula G.
Whiteoak, Christopher J. [1 ]
机构
[1] Sheffield Hallam Univ, Biomol Sci Res Ctr BMRC, Fac Hlth & Wellbeing, City Campus,Howard St, Sheffield S1 1WB, S Yorkshire, England
关键词
REDOX-NEUTRAL SYNTHESIS; PAUSON-KHAND REACTION; N BOND FORMATION; COBALT(III)-CATALYZED SYNTHESIS; INDOLE SYNTHESIS; EFFICIENT SYNTHESIS; TERMINAL ALKYNES; ACTIVATION; ANNULATION; AMIDATION;
D O I
10.1039/c7dt01980g
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Expansion of the synthetic chemists' toolbox is currently a topic of great interest, with successes providing access to novel compounds and more efficient routes towards new and known pharmaceuticals and agrochemicals. In this context, the development and application of first-row transition metal-catalysed C-H functionalisation protocols is seen as a key opportunity. This perspective provides a brief background of the discovery and application of high-valent cobalt-catalysis in C-H functionalisation, before detailing examples of recent advances in this field using the powerful [Cp*Co(CO)I-2] catalysts for both terminal couplings and heterocycle formation. Finally, a discussion on the detection and isolation of elusive reactive intermediates in high-valent cobalt-catalysed C-H functionalisation, shedding light on how these catalyst systems operate, will be provided.
引用
收藏
页码:9721 / 9739
页数:19
相关论文
共 118 条
[21]   TRANSITION-METAL COMPLEXES OF DIAZENES .32. FUNCTIONALIZATION OF AROMATIC AZO-COMPOUNDS BY THE COBALT-CATALYZED, REGIOSELECTIVE DOUBLE ADDITION OF TOLANE - 2,6-DISTILBENYLAZOBENZENES AND 2,3-DIHYDROCINNOLINES [J].
HALBRITTER, G ;
KNOCH, F ;
WOLSKI, A ;
KISCH, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (15-16) :1603-1605
[22]   Cobalt-Catalyzed Hydroformylation of Alkenes: Generation and Recycling of the Carbonyl Species, and Catalytic Cycle [J].
Hebrard, Frederic ;
Kalck, Philippe .
CHEMICAL REVIEWS, 2009, 109 (09) :4272-4282
[23]   C-H bond functionalization based on metal carbene migratory insertion [J].
Hu, Fangdong ;
Xia, Ying ;
Ma, Chen ;
Zhang, Yan ;
Wang, Jianbo .
CHEMICAL COMMUNICATIONS, 2015, 51 (38) :7986-7995
[24]   Microwave-Assisted Cp*CoIII-Catalyzed C-H Activation/Double C-N Bond Formation Reactions to Thiadiazine 1-Oxides [J].
Huang, Jiapian ;
Huang, Yangfei ;
Wang, Tao ;
Huang, Qin ;
Wang, Zhihua ;
Chen, Zhiyuan .
ORGANIC LETTERS, 2017, 19 (05) :1128-1131
[25]   Cobalt(III)-Catalyzed C-H Bond Amidation with Isocyanates [J].
Hummel, Joshua R. ;
Ellman, Jonathan A. .
ORGANIC LETTERS, 2015, 17 (10) :2400-2403
[26]   Cobalt(III)-Catalyzed Synthesis of Indazoles and Furans by C-H Bond Functionalization/Addition/Cyclization Cascades [J].
Hummel, Joshua R. ;
Ellman, Jonathan A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (01) :490-498
[27]   Stereoselective Synthesis of Tetrasubstituted Alkenes via a Cp*CoIII-Catalyzed C-H Alkenylation/Directing Group Migration Sequence [J].
Ikemoto, Hideya ;
Tanaka, Ryo ;
Sakata, Ken ;
Kanai, Motomu ;
Yoshino, Tatsuhiko ;
Matsunaga, Shigeki .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (25) :7156-7160
[28]   Pyrroloindolone Synthesis via a Cp*CoIII-Catalyzed Redox-Neutral Directed C-H Alkenylation/Annulation Sequence [J].
Ikemoto, Hideya ;
Yoshino, Tatsuhiko ;
Sakata, Ken ;
Matsunaga, Shigeki ;
Kanai, Motomu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (14) :5424-5431
[29]   INTRAMOLECULAR C-H BOND ACTIVATION IN AQUEOUS-SOLUTION - PREPARATION OF A UNIQUE COBALT(III)-ALKYL COMPLEX BY DEPROTONATION OF AN AGOSTIC INTERMEDIATE - CRYSTAL-STRUCTURE OF [COIII(DACODA-C(2))(H2O].2H2O [J].
KANAMORI, K ;
BRODERICK, WE ;
JORDAN, RF ;
WILLETT, RD ;
LEGG, JI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (22) :7122-7124
[30]   Factors determining the course and mechanisms of Grignard reactions. IV. The effect of metallic halides on the reaction of aryl Grignard reagents and organic halides [J].
Kharasch, MS ;
Fields, EK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1941, 63 :2316-2320