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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

Iron Catalyzed Cascade Protocol for the Synthesis of Pyrrolo[1, 2-a]quinoxalines: A Powerful Tool to Access Solid State Emissive Organic Luminophores

Iron Catalyzed Cascade Protocol for the Synthesis of Pyrrolo[1, 2‐a]quinoxalines: A Powerful Tool to Access Solid State Emissive Organic Luminophores

An economical and operationally simple method for the synthesis of pyrrolo[1, 2-a]quinoxalines has been developed via C−H activation of readily available arylacetic acids. The synthesized pyrrolo[1, 2-a]quinoxalines exhibit excellent fluorescent properties in solution and solid state.

[Full Paper]
Jatin J. Lade, Bhausaheb N. Patil, Pratima A. Sathe, Kamlesh S. Vadagaonkar, Prabhakar Chetti, Atul C. Chaskar
ChemistrySelect, August 16, 2017, https://doi.org/10.1002/slct.201701383 Read article

Ruthenium-Catalyzed, Keto-Directed, Site-Selective C–H Activation of Diverse Chromanones with Alkenes

Ruthenium‐Catalyzed, Keto‐Directed, Site‐Selective C–H Activation of Diverse Chromanones with Alkenes

A protocol for the synthesis of C5-olefinated 2-arylchromanones in a regio- and stereoselective fashion through the ruthenium-catalyzed oxidative coupling of diversified 2-arylchromanones with various alkenes through a keto-directed, site-selective C–H activation reaction is developed. IBO = isobornyl.

[Communication]
Manickam Bakthadoss, Polu Vijay Kumar, Tatiparthi Sushmitha Reddy
Eur. J. Org. Chem., August 15, 2017, https://doi.org/10.1002/ejoc.201700513 Read article

Activation, Deactivation and Reversibility in a Series of Homogeneous Iridium Dehydrogenation Catalysts

Activation, Deactivation and Reversibility in a Series of Homogeneous Iridium Dehydrogenation Catalysts

[Review]
Liam S. Sharninghausen, Robert H. Crabtree
Isr. J. Chem., August 10, 2017, https://doi.org/10.1002/ijch.201700048 Read article

Synthesis of Benzopyrans by Enolate-Directed Rhodium-Catalyzed Oxidative C−H Alkenylation of 1,3-Dicarbonyl Compounds

Synthesis of Benzopyrans by Enolate‐Directed Rhodium‐Catalyzed Oxidative C−H Alkenylation of 1,3‐Dicarbonyl Compounds

Celebrating diversity: 2-Aryl-1,3-dicarbonyl compounds are shown to be reactive in enolate-directed oxidative alkenylations for the synthesis of benzopyrans in good to excellent yields. Coupling of a diverse range of substrates to a variety of electron-deficient alkenes was efficiently achieved by rhodium catalysis. Furthermore, the scope of the reaction was broad with good functional group tolerance.

[Full Paper]
Hari Babu Bollikolla, Subrahmanyam Choppakatla, Naresh Polam, Vijaya Durga Thripuram, Suresh Reddy Chidipudi
Asian J. Org. Chem., August 09, 2017, https://doi.org/10.1002/ajoc.201700371 Read article

Amides as Weak Coordinating Groups in Proximal C–H Bond Activation

Amides as Weak Coordinating Groups in Proximal C–H Bond Activation

This microreview focuses on the role and utility of amides and anilides in directed, proximal C–H bond functionalization reactions.

[Microreview]
Riki Das, Gangam Srikanth Kumar, Manmohan Kapur
Eur. J. Org. Chem., August 08, 2017, https://doi.org/10.1002/ejoc.201700546 Read article

Iridium Halide Complexes [1,1-X2-8-SMe2-1,2,8-IrC2B9H10]2 (X = Cl, Br, I): Synthesis, Reactivity and Catalytic Activity

Iridium Halide Complexes [1,1‐X2‐8‐SMe2‐1,2,8‐IrC2B9H10]2 (X = Cl, Br, I): Synthesis, Reactivity and Catalytic Activity

Iridium halide complexes [1,1-X2-8-SMe2-1,2,8-IrC2B9H10]2 (X = Cl, Br, I) were synthesized by reaction of the cyclooctadiene derivative 1-cod-8-SMe2-1,2,8-IrC2B9H10 with anhydrous hydrohalic acids HX. These complexes have proven to be effective catalysts for the dimerization of alkynes and the reductive amination of aldehydes and ketones.

[Full Paper]
Alexander P. Molotkov, Mikhail M. Vinogradov, Alexey P. Moskovets, Olga Chusova, Sergey V. Timofeev, Vasilii A. Fastovskiy, Yulia V. Nelyubina, Alexander A. Pavlov, Denis A. Chusov, Dmitry A. Loginov
Eur. J. Inorg. Chem., August 01, 2017, https://doi.org/10.1002/ejic.201700498 Read article

Linear Selective C–H Bond Alkylation with Activated Olefins Catalyzed by Cp*CoIII

Linear Selective C–H Bond Alkylation with Activated Olefins Catalyzed by Cp*CoIII

[Communication]
Nagaraju Barsu, Balakumar Emayavaramban, Basker Sundararaju
Eur. J. Org. Chem., July 31, 2017, https://doi.org/10.1002/ejoc.201700696 Read article

Synthesis and Reactivity of 2-Arylquinazoline Halidoruthenacycles in Arylation Reactions

Synthesis and Reactivity of 2‐Arylquinazoline Halidoruthenacycles in Arylation Reactions

The halogen plays a role: Halogen ligands in quinazoline halidoruthenacycles have an impact on the equilibrium of halogen–acetate ligand exchange, which influences the reactivity towards the arylation process. Mechanistic studies reveal that quinazoline halidoruthenacycles undergo an arylation reaction in the presence of KOAc through a SET-type Ar−X cleavage.

[Full Paper]
Petra Kuzman, Franc Požgan, Anton Meden, Jurij Svete, Bogdan Štefane
ChemCatChem, July 27, 2017, https://doi.org/10.1002/cctc.201700494 Read article

Iron-Catalyzed C−C Bond Formation via Chelation-Assisted C−H Activation

Iron‐Catalyzed C−C Bond Formation via Chelation‐Assisted C−H Activation

[Review]
Naohiko Yoshikai
Isr. J. Chem., July 26, 2017, https://doi.org/10.1002/ijch.201700047 Read article

Direct Insight into Ethane Oxidative Dehydrogenation over Boron Nitrides

Direct Insight into Ethane Oxidative Dehydrogenation over Boron Nitrides

DOS and don'ts of dehydrogenation: In the dehydrogenation of alkanes, conventional metal-based catalysts enable the dissociation of O2 into dissociative oxygen species (DOS), and thereby the C−H bonds can be easily activated; however, DOS inevitably overoxidize the alkanes to CO2. Adsorbed O2 at the edges of boron nitride can abstract a hydrogen atom from ethane to deliver the corresponding alkene with 100 % selectivity (S).

[Communication]
Rui Huang, Bingsen Zhang, Jia Wang, Kuang-Hsu Wu, Wen Shi, Yajie Zhang, Yuefeng Liu, Anmin Zheng, Robert Schlögl, Dang Sheng Su
ChemCatChem, July 24, 2017, https://doi.org/10.1002/cctc.201700725 Read article

One-Pot Biocatalytic Double Oxidation of α-Isophorone for the Synthesis of Ketoisophorone

One‐Pot Biocatalytic Double Oxidation of α‐Isophorone for the Synthesis of Ketoisophorone

Design of an enzymatic cascade: For the first biocatalytic one-pot double oxidation of α-isophorone to ketoisophorone, variants of the self-sufficient P450cam-RhFRed with improved activity are combined with Cm-ADH10 from Candida magnoliae. The reaction shows a productivity of up to 1.4 g L−1 d−1.

[Full Paper]
Michele Tavanti, Fabio Parmeggiani, J. Rubén Gómez Castellanos, Andrea Mattevi, Nicholas J. Turner
ChemCatChem, July 24, 2017, https://doi.org/10.1002/cctc.201700620 Read article

Group 9 Transition Metal-Catalyzed C−H Halogenations

Group 9 Transition Metal‐Catalyzed C−H Halogenations

[Review]
Fabian Lied, Tuhin Patra, Frank Glorius
Isr. J. Chem., July 07, 2017, https://doi.org/10.1002/ijch.201700053 Read article

Synthesis and Biological Activity of Octaketides from the Cytosporone Family

Synthesis and Biological Activity of Octaketides from the Cytosporone Family

[Full Paper]
Max von Delius, Christine M. Le, Bernhard Ellinger, Maria Kuzikov, Sheraz Gul, Vy M. Dong
Isr. J. Chem., July 07, 2017, https://doi.org/10.1002/ijch.201700023 Read article

C–H Activation and Alkyne Annulation via Automatic or Intrinsic Directing Groups: Towards High Step Economy

C–H Activation and Alkyne Annulation via Automatic or Intrinsic Directing Groups: Towards High Step Economy

Express of direction: Directing group (DG) strategy is widely used for selective C–H functionalization. In this account, we described our efforts and recent advances focused on C–H activation and alkyne annulation. By using various automatic DGs (DGauto) and intrinsic DGs (DGin), diverse heterocycles and carbocycles can be obtained from simple building blocks or parent molecules with high step economy.

[Personal Account]
Liyao Zheng, Ruimao Hua
Chem. Rec., July 06, 2017, https://doi.org/10.1002/tcr.201700024 Read article

Convergent Synthesis of α-Branched Amines by Transition-Metal-Catalyzed C−H Bond Additions to Imines

Convergent Synthesis of α‐Branched Amines by Transition‐Metal‐Catalyzed C−H Bond Additions to Imines

[Review]
Joshua R. Hummel, Jonathan A. Ellman
Isr. J. Chem., June 29, 2017, https://doi.org/10.1002/ijch.201700021 Read article

Recent Applications of Rh- and Pd-Catalyzed C(sp3)–H Functionalization in Natural Product Total Synthesis

Recent Applications of Rh‐ and Pd‐Catalyzed C(sp3)–H Functionalization in Natural Product Total Synthesis

[Microreview]
Patrick B. Brady, Vikram Bhat
Eur. J. Org. Chem., June 26, 2017, https://doi.org/10.1002/ejoc.201700641 Read article

Unexpected Solvent Effects in the Isomerization of iPrPCPIr(η2-PhC≡CPh) to a 1-Iridaindene

Unexpected Solvent Effects in the Isomerization of iPrPCPIr(η2‐PhC≡CPh) to a 1‐Iridaindene

[Full Paper]
Miles Wilklow-Marnell, William W. Brennessel, William D. Jones
Isr. J. Chem., June 14, 2017, https://doi.org/10.1002/ijch.201700013 Read article

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