Literature DB >> 30033454

A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

Carlo Sambiagio1, David Schönbauer, Remi Blieck, Toan Dao-Huy, Gerit Pototschnig, Patricia Schaaf, Thomas Wiesinger, Muhammad Farooq Zia, Joanna Wencel-Delord, Tatiana Besset, Bert U W Maes, Michael Schnürch.   

Abstract

The present review is devoted to summarizing the recent advances (2015-2017) in the field of metal-catalysed group-directed C-H functionalisation. In order to clearly showcase the molecular diversity that can now be accessed by means of directed C-H functionalisation, the whole is organized following the directing groups installed on a substrate. Its aim is to be a comprehensive reference work, where a specific directing group can be easily found, together with the transformations which have been carried out with it. Hence, the primary format of this review is schemes accompanied with a concise explanatory text, in which the directing groups are ordered in sections according to their chemical structure. The schemes feature typical substrates used, the products obtained as well as the required reaction conditions. Importantly, each example is commented on with respect to the most important positive features and drawbacks, on aspects such as selectivity, substrate scope, reaction conditions, directing group removal, and greenness. The targeted readership are both experts in the field of C-H functionalisation chemistry (to provide a comprehensive overview of the progress made in the last years) and, even more so, all organic chemists who want to introduce the C-H functionalisation way of thinking for a design of straightforward, efficient and step-economic synthetic routes towards molecules of interest to them. Accordingly, this review should be of particular interest also for scientists from industrial R&D sector. Hence, the overall goal of this review is to promote the application of C-H functionalisation reactions outside the research groups dedicated to method development and establishing it as a valuable reaction archetype in contemporary R&D, comparable to the role cross-coupling reactions play to date.

Entities:  

Year:  2018        PMID: 30033454      PMCID: PMC6113863          DOI: 10.1039/c8cs00201k

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  822 in total

1.  Cobalt-Catalyzed Intramolecular Oxidative C(sp3)-H/N-H Carbonylation of Aliphatic Amides.

Authors:  Li Zeng; Shan Tang; Dan Wang; Yi Deng; Jeng-Lung Chen; Jyh-Fu Lee; Aiwen Lei
Journal:  Org Lett       Date:  2017-04-13       Impact factor: 6.005

2.  Diastereoselective [3+2] Annulation of Aromatic/Vinylic Amides with Bicyclic Alkenes through Cobalt-Catalyzed C-H Activation and Intramolecular Nucleophilic Addition.

Authors:  Parthasarathy Gandeepan; Pachaiyappan Rajamalli; Chien-Hong Cheng
Journal:  Angew Chem Int Ed Engl       Date:  2016-02-23       Impact factor: 15.336

3.  C-H activation: Good things come in threes.

Authors:  Marco Simonetti; Igor Larrosa
Journal:  Nat Chem       Date:  2016-11-22       Impact factor: 24.427

4.  Direct Aerobic Carbonylation of C(sp²)-H and C(sp³)-H Bonds through Ni/Cu Synergistic Catalysis with DMF as the Carbonyl Source.

Authors:  Xuesong Wu; Yan Zhao; Haibo Ge
Journal:  J Am Chem Soc       Date:  2015-04-09       Impact factor: 15.419

5.  Electronic Nature of Ketone Directing Group as a Key To Control C-2 vs C-4 Alkenylation of Indoles.

Authors:  Veeranjaneyulu Lanke; Kiran R Bettadapur; Kandikere Ramaiah Prabhu
Journal:  Org Lett       Date:  2016-10-13       Impact factor: 6.005

6.  Palladium-Catalyzed Decarboxylative ortho-Acylation of Benzamides with α-Oxocarboxylic Acids.

Authors:  Kun Jing; Jia-Ping Yao; Zhong-Yuan Li; Qi-Li Li; Hao-Sheng Lin; Guan-Wu Wang
Journal:  J Org Chem       Date:  2017-11-21       Impact factor: 4.354

7.  Mild Cobalt(III)-Catalyzed Allylative C-F/C-H Functionalizations at Room Temperature.

Authors:  Daniel Zell; Valentin Müller; Uttam Dhawa; Markus Bursch; Rubén Rubio Presa; Stefan Grimme; Lutz Ackermann
Journal:  Chemistry       Date:  2017-07-31       Impact factor: 5.236

8.  ortho-C-H Arylation of Benzoic Acids with Aryl Bromides and Chlorides Catalyzed by Ruthenium.

Authors:  Agostino Biafora; Thilo Krause; Dagmar Hackenberger; Florian Belitz; Lukas J Gooßen
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-21       Impact factor: 15.336

9.  Rhodium(III)-Catalyzed C-H Alkynylation of Ferrocenes with Hypervalent Iodine Reagents.

Authors:  Shao-Bo Wang; Qing Gu; Shu-Li You
Journal:  J Org Chem       Date:  2017-05-09       Impact factor: 4.354

10.  Rh(iii)-catalyzed C-H olefination of N-pentafluoroaryl benzamides using air as the sole oxidant.

Authors:  Yi Lu; Huai-Wei Wang; Jillian E Spangler; Kai Chen; Pei-Pei Cui; Yue Zhao; Wei-Yin Sun; Jin-Quan Yu
Journal:  Chem Sci       Date:  2015-01-08       Impact factor: 9.825

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  96 in total

1.  C─C Cleavage Approach to C─H Functionalization of Saturated Aza-Cycles.

Authors:  Jose B Roque; Yusuke Kuroda; Justin Jurczyk; Li-Ping Xu; Jin Su Ham; Lucas T Göttemann; Charis A Roberts; Donovon Adpressa; Josep Saurí; Leo A Joyce; Djamaladdin G Musaev; Charles S Yeung; Richmond Sarpong
Journal:  ACS Catal       Date:  2020-01-16       Impact factor: 13.084

Review 2.  Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry.

Authors:  Laura Buglioni; Fabian Raymenants; Aidan Slattery; Stefan D A Zondag; Timothy Noël
Journal:  Chem Rev       Date:  2021-08-10       Impact factor: 60.622

Review 3.  N-Heterocyclic Carbene Complexes in C-H Activation Reactions.

Authors:  Qun Zhao; Guangrong Meng; Steven P Nolan; Michal Szostak
Journal:  Chem Rev       Date:  2020-01-22       Impact factor: 60.622

4.  Ligand-Enabled Pd(II)-Catalyzed C(sp3)-H Lactonization Using Molecular Oxygen as Oxidant.

Authors:  Shaoqun Qian; Zi-Qi Li; Minyan Li; Steven R Wisniewski; Jennifer X Qiao; Jeremy M Richter; William R Ewing; Martin D Eastgate; Jason S Chen; Jin-Quan Yu
Journal:  Org Lett       Date:  2020-04-24       Impact factor: 6.005

5.  Discovery, Total Synthesis, and SAR of Anaenamides A and B: Anticancer Cyanobacterial Depsipeptides with a Chlorinated Pharmacophore.

Authors:  David A Brumley; Sarath P Gunasekera; Qi-Yin Chen; Valerie J Paul; Hendrik Luesch
Journal:  Org Lett       Date:  2020-05-16       Impact factor: 6.005

6.  Finding Opportunities from Surprises and Failures. Development of Rhodium-Stabilized Donor/Acceptor Carbenes and Their Application to Catalyst-Controlled C-H Functionalization.

Authors:  Huw M L Davies
Journal:  J Org Chem       Date:  2019-10-10       Impact factor: 4.354

7.  Cobalt-Catalyzed C-H Activation/Annulation of Benzamides with Fluorine-Containing Alkynes: A Route to 3- and 4-Fluoroalkylated Isoquinolinones.

Authors:  Tatsuya Kumon; Jianyan Wu; Miroku Shimada; Shigeyuki Yamada; Tomohiro Agou; Hiroki Fukumoto; Toshio Kubota; Gerald B Hammond; Tsutomu Konno
Journal:  J Org Chem       Date:  2021-03-16       Impact factor: 4.354

8.  Exploiting in situ NMR to monitor the formation of a metal-organic framework.

Authors:  Corey L Jones; Colan E Hughes; Hamish H-M Yeung; Alison Paul; Kenneth D M Harris; Timothy L Easun
Journal:  Chem Sci       Date:  2020-11-20       Impact factor: 9.825

9.  Site-selective aqueous C-H acylation of tyrosine-containing oligopeptides with aldehydes.

Authors:  Marcos San Segundo; Arkaitz Correa
Journal:  Chem Sci       Date:  2020-10-06       Impact factor: 9.825

Review 10.  Direct Photocatalyzed Hydrogen Atom Transfer (HAT) for Aliphatic C-H Bonds Elaboration.

Authors:  Luca Capaldo; Davide Ravelli; Maurizio Fagnoni
Journal:  Chem Rev       Date:  2021-08-06       Impact factor: 60.622

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