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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

Macrolide Synthesis through Intramolecular Oxidative Cross-Coupling of Alkenes

Macrolide Synthesis through Intramolecular Oxidative Cross‐Coupling of Alkenes

Two pair: A RhIII-catalyzed intramolecular oxidative cross-coupling between double bonds for the synthesis of macrolides is described. Under the optimized conditions, macrocycles containing a diene moiety can be formed in reasonable yields and with excellent chemo- and stereoselectivity. This provides efficient access to macrocyclic compounds containing 1,3-conjugated dienes.

[Communication]
Bing Jiang, Meng Zhao, Shu-Sen Li, Yun-He Xu, Teck-Peng Loh
Angew. Chem. Int. Ed., December 12, 2017, https://doi.org/10.1002/anie.201710601 Read article

Highly Selective Manganese(I)/Lewis Acid Cocatalyzed Direct C−H Propargylation Using Bromoallenes

Highly Selective Manganese(I)/Lewis Acid Cocatalyzed Direct C−H Propargylation Using Bromoallenes

Proper(gylation)! In a highly selective manganese(I)/Lewis acid cocatalyzed direct C−H propargylation, BPh3 not only promotes the reactivity, but also enhances the selectivity. Secondary, tertiary, and even quaternary carbon centers at the propargylic position could be directly constructed. The reactivity of the manganese catalyst in this reaction is unique among transition metal catalysts.

[Communication]
Can Zhu, Jonas Luca Schwarz, Sara Cembellín, Steffen Greßies, Frank Glorius
Angew. Chem. Int. Ed., December 08, 2017, https://doi.org/10.1002/anie.201710835 Read article

Rhodium-Catalyzed Alkenyl C−H Activation and Oxidative Coupling with Allylic Alcohols

Rhodium‐Catalyzed Alkenyl C−H Activation and Oxidative Coupling with Allylic Alcohols

Oxidative coupling of allylic alcohols: [Cp*RhCl2]2 was demonstrated to catalyze the oxidative coupling of alkenylpyridines with allylic alcohols through alkenyl C−H activation in the presence of AgOTf and AgOAc to afford β-alkenyl ketones and aldehydes in moderate to good yields.

[Full Paper]
Rui Yan, Zhong-Xia Wang
Asian J. Org. Chem., December 07, 2017, https://doi.org/10.1002/ajoc.201700515 Read article

Dissymmetrization of Benzothiadiazole by Direct C–H Arylation: A Way to Symmetrical and Unsymmetrical Elongated π-Conjugated Molecules

Dissymmetrization of Benzothiadiazole by Direct C–H Arylation: A Way to Symmetrical and Unsymmetrical Elongated π‐Conjugated Molecules

The mono-substitution of benzothiadiazole (Bz) is of high interest for constructing donor–acceptor molecules based on thiophene (Th) and an electron-donating group (EDG). Dissymmetrization of benzothiadiazole has been realized through phosphine-free direct arylation, and subsequent reactions led to either symmetrical or unsymmetrical chromophores.

[Full Paper]
Chunxiang Dall'Agnese, Daniel Hernández Maldonado, Damien Le Borgne, Kathleen I. Moineau-Chane Ching
Eur. J. Org. Chem., December 06, 2017, https://doi.org/10.1002/ejoc.201701382 Read article

Palladium-Catalyzed ortho-Alkoxylation of Tertiary Benzamides: H2SO4 as an Effective Additive

Palladium‐Catalyzed ortho‐Alkoxylation of Tertiary Benzamides: H2SO4 as an Effective Additive

H2SO4 as an effective additive: A direct synthesis of aryl ethers has been developed via a palladium-catalyzed alkoxylation of tertiary benzamides with alcohols. H2SO4 was found to be a key additive, which could greatly enhance the catalytic reactivity of the palladium catalyst.

[Communication]
Fang-Cheng Qiu, Qi Xie, Bing-Tao Guan
Asian J. Org. Chem., November 14, 2017, https://doi.org/10.1002/ajoc.201700525 Read article

Iron and Single Electron Transfer: All is in the Ligand

Iron and Single Electron Transfer: All is in the Ligand

[Review]
Marine Desage-El Murr, Louis Fensterbank, Cyril Ollivier
Isr. J. Chem., November 08, 2017, https://doi.org/10.1002/ijch.201700061 Read article

Elemental-Sulfur-Promoted C(sp3)−H Activation of Methyl Heteroarenes Leading to Thioamides

Elemental‐Sulfur‐Promoted C(sp3)−H Activation of Methyl Heteroarenes Leading to Thioamides

Release Me2N(ight)! Sulfur-promoted C(sp3)−H activation of methyl heteroarenes generates bioactive thioamides. This transformation successfully furnished a series of heterocyclic thioamides with excellent yields and it could be conducted on gram scale with good reaction efficiency. Mechanistic studies showed that methyl heteroarenes reacted with dimethylamine released from DMF to form the desired thioamide.

[Communication]
Jianming Liu, Shanshan Zhao, Xuyang Yan, Yanyan Zhang, Shufang Zhao, Kelei Zhuo, Yuanyuan Yue
Asian J. Org. Chem., October 18, 2017, https://doi.org/10.1002/ajoc.201700532 Read article

RuII-Catalyzed ortho-Sulfonamidation of α-Tetralones with Sulfonyl Azides and Synthesis of Sivelestat by Aromatic C−H Activation

RuII‐Catalyzed ortho‐Sulfonamidation of α‐Tetralones with Sulfonyl Azides and Synthesis of Sivelestat by Aromatic C−H Activation

Amide other reactions: A method has been developed for the sulfonamidation of α-tetralones and 1,4-naphthoquinones by using sulfonyl azides and a RuII/AgI catalytic system (see scheme; DCE=1,2-dichloroethane). Tetralones underwent C−H bond functionalization exclusively at the ortho position, whereas 1,4-addition was the primary reaction for 1,4-naphthoquinone. This highly regioselective approach was also used to synthesize sivelestat, an inhibitor of human neutrophil elastase.

[Full Paper]
Medikonda V. Krishna Rao, Keesari Nagarjuna Reddy, Balasubramaniam Sridhar, Basi V. Subba Reddy
Asian J. Org. Chem., October 18, 2017, https://doi.org/10.1002/ajoc.201700356 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

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

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