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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

Access to (Hetero)arylated Selenophenes via Palladium-catalysed Stille, Negishi or Suzuki Couplings or C−H Bond Functionalization Reaction

Access to (Hetero)arylated Selenophenes via Palladium‐catalysed Stille, Negishi or Suzuki Couplings or C−H Bond Functionalization Reaction

Selenophenes stereotypes: The progress and substrate scope of the palladium catalyzed synthesis of both C2- and C3-arylated selenophenes are summarized in this Review—from Stille, Suzuki, and Negishi coupling through to C−H bond activation

[Review]
Aymen Skhiri, Ridha Ben Salem, Jean-François Soulé, Henri Doucet
ChemCatChem, June 22, 2017, https://doi.org/10.1002/cctc.201700256 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

Facile Construction of Quinoline-2-carboxylate Esters through Aerobic Oxidation of Alkyl 4-anilinocrotonates Induced by a Radical Cation Salt

Facile Construction of Quinoline‐2‐carboxylate Esters through Aerobic Oxidation of Alkyl 4‐anilinocrotonates Induced by a Radical Cation Salt

Queen′o′Lines: A facile construction of quinoline-2-carboxylate esters through an aerobic oxidation of alkyl 4-anilinocrotonates is described. This reaction provides a new way to construct the pharmaceutically relevant quinoline skeleton, avoiding harsh reaction conditions and tedious starting material synthesis.

[Communication]
Xiaodong Jia, Pengfei Li, Yu Shao, Yu Yuan, Wentao Hou, Xiaofei Liu, Xuewen Zhang, Honghe Ji
Chem. Asian J., June 08, 2017, https://doi.org/10.1002/asia.201700560 Read article

Water as a Hydroxy Source in a RhIII-Catalyzed Directed C−H Hydroxylation of 2-Arylpyridines

Water as a Hydroxy Source in a RhIII‐Catalyzed Directed C−H Hydroxylation of 2‐Arylpyridines

Three and easy: The directed C−H hydroxylation of 2-arylpyridines was efficiently catalyzed by [(RhCp*Cl2)2] and AgF in 38–93 % yield. Mechanistic investigation indicated that the 2-(pyridin-2-yl)phenol O atom was transferred from water.

[Full Paper]
Kiseong Kim, Jaeyong Hyun, Jin Kim, Hyunwoo Kim
Asian J. Org. Chem., June 07, 2017, https://doi.org/10.1002/ajoc.201700196 Read article

Synthesis of Polycyclic Amides via Tandem RhIII-Catalyzed C−H Activation and Annulation from Dioxazolones and Alkynes

Synthesis of Polycyclic Amides via Tandem RhIII‐Catalyzed C−H Activation and Annulation from Dioxazolones and Alkynes

From straight lines to rings: A highly efficient synthesis of polycyclic amides by a RhIII-catalyzed cascade cyclization of 3-phenyl-1,4,2-dioxazol-5-one and diphenylacetylene has been developed. This one-pot strategy expanded the application scope of directing groups to dioxazolones.

[Communication]
Guo-Tai Zhang, Lin Dong
Asian J. Org. Chem., June 01, 2017, https://doi.org/10.1002/ajoc.201700140 Read article

Rhenium-Catalyzed Annulation Reactions

Rhenium‐Catalyzed Annulation Reactions

The unique properties of rhenium, such as its low electronegativity and its ability to activate C–H and C–C bonds, enable a series of atom- and step-economical annulation reactions from simple substrates. This Microreview aims to summarize the impressive progress in this field.

[Microreview]
Guoliang Mao, Qiang Huang, Congyang Wang
Eur. J. Org. Chem., May 23, 2017, https://doi.org/10.1002/ejoc.201700285 Read article

Uncatalyzed C−H Amination of Aromatic Compounds under Unusually Mild Conditions with Negative Enthalpies of Activation

Uncatalyzed C−H Amination of Aromatic Compounds under Unusually Mild Conditions with Negative Enthalpies of Activation

Blowing hot and cold: Chemists are used to using heat to activate sluggish reactions; however, cooling is more appropriate in a new amination reaction of aromatic compounds, owing to strongly negative enthalpies of activation.

[Full Paper]
Heinz Langhals, Moritz Eberspächer, Peter Mayer
Asian J. Org. Chem., May 08, 2017, https://doi.org/10.1002/ajoc.201700106 Read article

Silver-Catalyzed Direct C6–H Arylation of Purines and Purine Nucleosides with Arylboronic Acids

Silver‐Catalyzed Direct C6–H Arylation of Purines and Purine Nucleosides with Arylboronic Acids

An efficient protocol for the direct C6–H arylation of purines and purine nucleosides is described under the catalysis of silver nitrate and under ambient conditions. A wide assortment of purines and arylboronic acids can be employed in this process to afford C6-arylpurines and purine nucleosides with high regioselectivity. TFA = trifluoroacetic acid; DCE = 1,2-dichloroethane.

[Communication]
Miao Tian, Mingwu Yu, Tingting Shi, Junbin Hu, Shunlai Li, Jiaxi Xu, Ning Chen, Hongguang Du
Eur. J. Org. Chem., April 26, 2017, https://doi.org/10.1002/ejoc.201700406 Read article

Recent Progress in Decarboxylative Oxidative Cross-Coupling for Biaryl Synthesis

Recent Progress in Decarboxylative Oxidative Cross‐Coupling for Biaryl Synthesis

Developing efficient and selective routes for biaryl synthesis is of great interest. Decarboxylative oxidative coupling is appealing, because both substrate classes are readily available, and only CO2 and H2O are formed as side products. Furthermore, the carboxyl group offers a site for selective transformations. This review details decarboxylative oxidative coupling from 2008 to the present.

[Microreview]
Gregory J. P. Perry, Igor Larrosa
Eur. J. Org. Chem., April 26, 2017, https://doi.org/10.1002/ejoc.201700121 Read article

Metal-Free, TBHP-Mediated, [3+2+1]-Type Intermolecular Cycloaddition Reaction: Synthesis of Pyrimidines from Amidines, Ketones, and DMF through C(sp3)−H Activation

Metal‐Free, TBHP‐Mediated, [3+2+1]‐Type Intermolecular Cycloaddition Reaction: Synthesis of Pyrimidines from Amidines, Ketones, and DMF through C(sp3)−H Activation

Born metal-free: A metal-free synthesis of pyrimidines through a [3+2+1]-type intermolecular cycloaddition reaction with C(sp3)−H activation features sustainable oxidants, readily available substrates, and high atom and step economies.

[Full Paper]
Lv-Yin Zheng, Wei Guo, Xiao-Lin Fan
Asian J. Org. Chem., April 21, 2017, https://doi.org/10.1002/ajoc.201700105 Read article

Recent Advances in Functionalization of α-C(sp3)–H Centres in Inactivated Ethers through Cross Dehydrogenative Coupling

Recent Advances in Functionalization of α‐C(sp3)–H Centres in Inactivated Ethers through Cross Dehydrogenative Coupling

C–H activation in saturated ethers followed by functionalization with various coupling partners under oxidative conditions has been an area of significant interest. This microreview sheds light on C–C and C–heteroatom bond formation in these inactivated ethers.

[Microreview]
Aanchal Batra, Paramjit Singh, Kamal Nain Singh
Eur. J. Org. Chem., April 20, 2017, https://doi.org/10.1002/ejoc.201700341 Read article

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