☆ 4.7 Review

Advances in allylic and benzylic C-H bond functionalization enabled by metallaphotoredox catalysis

CHEMICAL COMMUNICATIONS (2021)

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Review Chemistry, Multidisciplinary

Nickel-Catalyzed C-Heteroatom Cross-Coupling Reactions under Mild Conditions via Facilitated Reductive Elimination

Chen Zhu et al.

Summary: The formation of C-heteroatom bonds through recent advances in homo- and heterogeneous Ni-catalyzed reactions under mild conditions is attractive due to sustainability and practicability. The generation of Ni-III and excited Ni-II intermediates enables mild cross-couplings, leading to the development of various catalytic systems involving photoredox and nickel dual catalysis, photoexcited nickel catalysis, electro and nickel dual catalysis, and heterogeneous photoredox and nickel dual catalysis using different materials.

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C(sp3)-H methylation enabled by peroxide photosensitization and Ni-mediated radical coupling

Aristidis Vasilopoulos et al.

Summary: The research presents a synthetic method that allows for direct methylation of C(sp(3))-H bonds in drug-like molecules and pharmaceutical building blocks, leading to changes in potency, selectivity, and metabolic stability.

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Article Multidisciplinary Sciences

Photocatalytic three-component asymmetric sulfonylation via direct C(sp3)-H functionalization

Shi Cao et al.

Summary: The study demonstrates the use of a dual asymmetric photocatalyst leading to the development of asymmetric sulfonylation involving direct functionalization of cycloalkanes, alkanes, toluene derivatives or ethers.

NATURE COMMUNICATIONS (2021)

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Review Chemistry, Organic

Photoredox catalysis in nickel-catalyzed C-H functionalization

Lusina Mantry et al.

Summary: C-H functionalization has emerged as a powerful strategy in organic synthesis, offering improved economy and unique reaction pathways compared to traditional methods. Nickel catalysts in photoredox C-H functionalization have garnered significant attention for their relative earth-abundance and cost-effectiveness.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Multidisciplinary Sciences

Asymmetric benzylic C(sp3)-H acylation via dual nickel and photoredox catalysis

Leitao Huan et al.

Summary: The study presents an asymmetric benzylic C-H acylation reaction using nickel and photoredox dual catalysis, with carboxylic acids as acyl surrogates, to synthesize high enantioselective alpha-aryl ketones. This method can convert various feedstock carboxylic acids and simple alkylarenes into valuable alpha-aryl ketones, showcasing potential applications in gram-scale synthesis and late-stage modification of medicinally relevant molecules. Mechanistic studies suggest that a bromine-radical-mediated C-H activation strategy plays a crucial role in this reaction.

NATURE COMMUNICATIONS (2021)

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Article Chemistry, Physical

Stereo- and Enantioselective Benzylic C-H Alkenylation via Photoredox/Nickel Dual Catalysis

Xiaokai Cheng et al.

Summary: A stereo- and enantioselective benzylic C-H alkenylation via photoredox/nickel catalysis has been developed, allowing for smooth cross-coupling reactions of readily available alkylbenzenes and alkenyl bromides, even with complicated molecules. The reaction conditions are mild with good functional group tolerance, yielding chiral allylic compounds with high ee and E/Z ratio. Additionally, a triplet-energy-transfer-inhibiting strategy has been developed for stereoselective synthesis of alkenes under visible-light photocatalysis, with the coordination pattern of nickel with chiral bis-imidazoline ligand elucidated based on experiments and X-ray diffraction.

ACS CATALYSIS (2021)

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Review Chemistry, Physical

Photoinduced intermolecular hydrogen atom transfer reactions in organic synthesis

Hui Cao et al.

Summary: HAT technology provides a simple method to generate open-shell radical intermediates from R-H bonds, while photoinduced intermolecular HAT reactions have seen significant developments in efficiency, selectivity, and versatility, offering new opportunities for green synthesis.

CHEM CATALYSIS (2021)

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C-H activation

Torben Rogge et al.

Summary: C-H activation has emerged as a powerful platform for molecular syntheses in various fields including natural product syntheses, pharmaceutical industries, and material sciences. This Primer summarizes best practices for experimental set-up, data deposition, and key developments in C-H activation, as well as discussing its applications and limitations.

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Benzylic C(sp3)-C(sp2) cross-coupling of indoles enabled by oxidative radical generation and nickel catalysis

Weonjeong Kim et al.

Summary: A unique functionalization strategy for a benzylic C(sp(3))-H bond has been developed based on the facile oxidation event of indole substrates. The method utilizes mild conditions and exhibits a wide substrate scope for both substituted indoles and C(sp(2))-based reaction counterparts. Competitive hydrogen atom transfer processes, commonly seen in conventional methods, are not involved in the product formation process of this developed strategy.

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Article Chemistry, Multidisciplinary

Dehydrogenative Coupling of Benzylic and Aldehydic C-H Bonds

Tairin Kawasaki et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Review Chemistry, Organic

When metal-catalyzed C-H functionalization meets visible-light photocatalysis

Lucas Guillemard et al.

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Catalytic Allylation of Aldehydes Using Unactivated Alkenes

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Manganese-Catalyzed Oxidative Azidation of C(sp3)-H Bonds under Electrophotocatalytic Conditions

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Synthesis of unsymmetrical ketones by applying visible-light benzophenone/nickel dual catalysis for direct benzylic acylation

Patricia E. Podsiadly et al.

CHEMICAL COMMUNICATIONS (2020)

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The Dual Role of Benzophenone in Visible-Light/Nickel Photoredox-Catalyzed C-H Arylations: Hydrogen-Atom Transfer and Energy Transfer

Abhishek Dewanji et al.

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Carboxylation of Benzylic and Aliphatic C-H Bonds with CO2 Induced by Light/Ketone/Nickel

Naoki Ishida et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

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Enantioselective benzylic C-H arylation via photoredox and nickel dual catalysis

Xiaokai Cheng et al.

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Photocatalytic regio- and stereoselective C(sp3)-H functionalization of benzylic and allylic hydrocarbons as well as unactivated alkanes

Yanjun Li et al.

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3d Transition Metals for C-H Activation

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Catalytic asymmetric allylation of aldehydes with alkenes through allylic C(sp3)-H functionalization mediated by organophotoredox and chiral chromium hybrid catalysis

Harunobu Mitsunuma et al.

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Transition-Metal-Catalyzed Selective Functionalization of C(sp(3))-H Bonds in Natural Products

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Direct Cross-Coupling of Allylic C(sp(3))-H Bonds with Aryl- and Vinylbromides by Combined Nickel and Visible-Light Catalysis

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One-Pot Photomediated Giese Reaction/Friedel-Crafts Hydroxyalkylation/Oxidative Aromatization To Access Naphthalene Derivatives from Toluenes and Enones

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

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sp(3) C-H Arylation and Alkylation Enabled by the Synergy of Triplet Excited Ketones and Nickel Catalysts

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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

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Aqueous Benzylic C-H Trifluoromethylation for Late-Stage Functionalization

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Diastereoselective Allylation of Aldehydes by Dual Photoredox and Chromium Catalysis

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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

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Direct arylation of strong aliphatic C-H bonds

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NATURE (2018)

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Selective functionalization of methane, ethane, and higher alkanes by cerium photocatalysis

Anhua Hu et al.

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Direct C-C Bond Formation from Alkanes Using Ni-Photoredox Catalysis

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Cooperation of a Nickel-Bipyridine Complex with Light for Benzylic C-H Arylation of Toluene Derivatives

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Direct C(sp3)-H Cross Coupling Enabled by Catalytic Generation of Chlorine Radicals

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Ligand-Controlled C(sp3)-H Arylation and Olefination in Synthesis of Unnatural Chiral α-Amino Acids

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Catalytic Functionalization of C(sp2)-H and C(sp3)-H Bonds by Using Bidentate Directing Groups

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