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C–H Activation

The possibility of direct introduction of a new functionality (or a new C–C bond) via direct C–H bond transformation is a highly attractive strategy in covalent synthesis. The range of substrates is virtually unlimited, including hydrocarbons, complex organic compounds of small molecular weight, and synthetic and biological polymers. Below is a list of recent articles on this topic. For a review, see

  1. Xiao Chen, Keary M. Engle, Dong-Hui Wang, Jin-Quan Yu*
    Palladium(II)-Catalyzed C–H Activation/C–C Cross-Coupling Reactions: Versatility and Practicality
    Angew. Chem. 2009, 121, 5196–5217; Angew. Chem. Int. Ed. 2009, 48, 5094–5115

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Recent Articles

Frustrated Lewis Pair Mediated Csp3−H Activation

Frustrated Lewis Pair Mediated Csp3−H Activation

Frustrated Lewis pair chemistry: The activation of a Csp3−H bond by a frustrated Lewis pair (FLP) mechanism to generate unusual N, B heterocycles is reported.

[Communication]
Étienne Rochette, Marc-André Courtemanche, Frédéric-Georges Fontaine
Chem. Eur. J., February 21, 2017, DOI: 10.1002/chem.201700390. Read article

Arylation of N-Methyl-2-oxindole with Arylboronic Acids in Water Catalyzed by Palladium(II) Pincer Complexes with a Low Catalyst Loading

Arylation of N‐Methyl‐2‐oxindole with Arylboronic Acids in Water Catalyzed by Palladium(II) Pincer Complexes with a Low Catalyst Loading

Power of palladium pincer complex: Two new PdII ONO pincer complexes are utilized efficiently as homogeneous catalysts for the site-selective C3-arylation of N-methyl-2-oxindole with arylboronic acids at room temperature in aqueous media to yield a series of 3-aryl-N-methyl-2-oxindoles.

[Communication]
Arumugam Vignesh, Werner Kaminsky, Nallasamy Dharmaraj
ChemCatChem, February 20, 2017, DOI: 10.1002/cctc.201601411. Read article

Synthesis of Active Hexafluoroisopropyl Benzoates through Hydrogen-Bond-Enabled Palladium(II)-Catalyzed C−H Alkoxycarbonylation Reaction

Synthesis of Active Hexafluoroisopropyl Benzoates through Hydrogen‐Bond‐Enabled Palladium(II)‐Catalyzed C−H Alkoxycarbonylation Reaction

Let's get active: The title reaction of aryl silanes to deliver active hexafluoroisopropyl (HFIP) benzoate esters features high selectivity and good functional-group tolerance. This method yields products bearing two independently modifiable sites. NMR studies reveal the presence of hydrogen bonding between HFIP and a pyrimidine nitrogen atom of the directing group (DG), and it is thought to be crucial for the success of this alkoxycarbonylation reaction.

[Communication]
Yang Wang, Vladimir Gevorgyan
Angew. Chem. Int. Ed., February 17, 2017, DOI: 10.1002/anie.201611757. Read article

Modern Synthetic Avenues for the Preparation of Functional Fluorophores

Modern Synthetic Avenues for the Preparation of Functional Fluorophores

Functional fluorophores enable the fast and accurate profiling of specific biomolecules but these sophisticated structures are often difficult to access through conventional synthetic strategies. Recent advances in the design, preparation, and fine-tuning of fluorophores by means of multicomponent reactions, C−H activation processes, cycloadditions, and biomolecule-based chemical transformations are discussed.

[Minireview]
Fabio de Moliner, Nicola Kielland, Rodolfo Lavilla, Marc Vendrell
Angew. Chem. Int. Ed., February 17, 2017, DOI: 10.1002/anie.201609394. Read article

Template-Assisted meta-C−H Alkylation and Alkenylation of Arenes

Template‐Assisted meta‐C−H Alkylation and Alkenylation of Arenes

On target: Pyrimidine-based, template-assisted meta-C−H alkylation and alkenylation with allyl alcohols and protected allyl alcohols has been developed. Sulfonyl, carbonyl, and phosphonyl esters were used as linkers between the directing group (DG) and target meta-C−H bond of arene.

[Communication]
Sukdev Bag, Ramasamy Jayarajan, Rahul Mondal, Debabrata Maiti
Angew. Chem. Int. Ed., February 16, 2017, DOI: 10.1002/anie.201611360. Read article

C(sp3)–H Bond Activation Induced by Monohydroborane Coordination at an Iridium(III)–Phosphoramidate Complex

C(sp3)–H Bond Activation Induced by Monohydroborane Coordination at an Iridium(III)–Phosphoramidate Complex

Two is better than one to generate cyclometalated Cp*IrIII phosphoramidate complexes by sequential intramolecular B–H and C(sp3)–H bond-activation events. Such complexes represent a first step in an overall Ir-catalyzed process for organophosphate functionalization. Cp* = pentamethylcyclopentadienyl; Mes = mesityl.

[Communication]
Marcus W. Drover, Cheyenne J. Christopherson, Laurel L. Schafer, Jennifer A. Love
Eur. J. Inorg. Chem., February 13, 2017, DOI: 10.1002/ejic.201601518. Read article

Iodine-Mediated Sulfonylation of Quinoline N-Oxides: a Mild and Metal-Free One-Pot Synthesis of 2-Sulfonyl Quinolines

Iodine‐Mediated Sulfonylation of Quinoline N‐Oxides: a Mild and Metal‐Free One‐Pot Synthesis of 2‐Sulfonyl Quinolines

Only a little bit of iodine: A synthetic strategy for an iodine-mediated sulfonylation of quinoline N-oxides has been developed. A wide variety of 2-sulfonyl quinoline derivatives were synthesized by reacting various quinoline N-oxides with different sodium sulfinates in the presence of sub-stoichiometric amounts of I2 in one pot, after 2 h at room temperature.

[Communication]
Wen-Kai Fu, Kai Sun, Chen Qu, Xiao-Lan Chen, Ling-Bo Qu, Wen-Zhu Bi, Yu-Fen Zhao
Asian J. Org. Chem., February 08, 2017, DOI: 10.1002/ajoc.201700001. Read article

Porphyrin-Catalyzed Photochemical C–H Arylation of Heteroarenes

Porphyrin‐Catalyzed Photochemical C–H Arylation of Heteroarenes

Porphyrins are suitable photoredox catalysts for the direct C–H arylation of heteroarenes with aryl diazonium salts. The reaction involves photoelectron transfer from a porphyrin in its exited state to a diazonium salt.

[Communication]
Katarzyna Rybicka-Jasińska, Burkhard König, Dorota Gryko
Eur. J. Org. Chem., January 27, 2017, DOI: 10.1002/ejoc.201601518. Read article

Metal-Catalysed Azidation of Organic Molecules

Metal‐Catalysed Azidation of Organic Molecules

The azide moiety is a desirable functionality in organic molecules, useful in a variety of transformations such as triazole synthesis, aziridination, C–H bond amination, isocyanate synthesis, the Staudinger reaction etc. This review highlights metal-catalysed azidation, which provides shorter routes to a variety of organic molecules of interest, with a focus on substrate scopes and mechanisms.

[Microreview]
Monalisa Goswami, Bas de Bruin
Eur. J. Org. Chem., December 22, 2016, DOI: 10.1002/ejoc.201601390. Read article

Mild Palladium Catalyzed ortho C-H Bond Functionalizations of Aniline Derivatives

Mild Palladium Catalyzed ortho C‐H Bond Functionalizations of Aniline Derivatives

In this account we summarize and discuss synthetic solutions for the realization of palladium catalyzed, ortho-directed C-H functionalization of aniline derivatives under mild reaction conditions for the construction of new carbon-carbon and carbon-oxygen bonds.

[Personal Account]
Orsolya Tischler, Balázs Tóth, Zoltán Novák
The Chemical Record, August 09, 2016, DOI: 10.1002/tcr.201600059. Read article

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