4.6 Review

Non-Noble Metal-Catalyzed Carbonylative Multi-Component Reactions

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Article Chemistry, Organic

Cobalt-Catalyzed Four-Component Carbonylation of Methylareneswith Ethylene and Alcohols

Jian-Xing Xu et al.

Summary: The developed cobalt-catalyzed multicomponent carbonylative reaction offers a cost-effective method to synthesize gamma-aryl carboxylic acid esters directly from readily available raw materials, which have wide applications in FDA-approved drugs.

JOURNAL OF ORGANIC CHEMISTRY (2022)

Article Chemistry, Multidisciplinary

Copper-catalyzed carbonylative catenation of olefins: Direct synthesis of γ-boryl esters

Fu-Peng Wu et al.

Summary: Carbonylation reactions are important in contemporary organic chemistry as they provide access to compounds with carbon monoxide or methyl groups. We report a copper-catalyzed carbonylative catenation and borylation reaction and propose a possible reaction mechanism.
Article Chemistry, Multidisciplinary

Nickel-Catalyzed Four-Component Carbonylation of Ethers and Olefins: Direct Access to γ-Oxy Esters and Amides

Le-Cheng Wang et al.

Summary: Here, we report a novel carbonylation reaction method for olefins using ethers as substrates under low CO pressure. This method allows for the synthesis of diverse gamma-oxy-substituted esters and amides with high functional group tolerance. Additionally, it enables the straightforward synthesis of Naftidrofuryl, a medicine for the treatment of cerebrovascular disease.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Article Chemistry, Physical

Visible light-induced perfluoroalkylative carbonylation of unactivated alkenes

Youcan Zhang et al.

Summary: A visible light-mediated perfluoroalkylative carbonylation method using a photocatalyst system based on copper and BINAP has been developed. The method enables the synthesis of functionalized b-perfluoroalkyl esters and amides with high efficiency and excellent selectivity.

JOURNAL OF CATALYSIS (2022)

Article Chemistry, Multidisciplinary

Copper-catalyzed hydroaminocarbonylation of benzylidenecyclopropanes: synthesis of γ,δ-unsaturated amides

Hui-Qing Geng et al.

Summary: In this study, we have developed a copper-catalyzed hydroaminocarbonylation of benzylidenecyclopropanes under relatively mild conditions. A series of gamma,delta-unsaturated amides with a broad range of functional groups were obtained in moderate to good yields. Both dialkyl-substituted and monoalkyl-substituted hydroxylamine derivatives can be applied in this transformation to give the corresponding tertiary and secondary amides successfully.

CHEMICAL COMMUNICATIONS (2022)

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Ligand-Controlled Copper-Catalyzed Regiodivergent Carbonylative Synthesis of α-Amino Ketones and α-Boryl Amides from Imines and Alkyl Iodides

Fu-Peng Wu et al.

Summary: Regioselective transformation is achieved in copper-catalyzed regiodivergent borocarbonylation of imines with alkyl iodides, with different ligands controlling the regioselectivity to produce either alpha-amino ketones or alpha-boryl amides selectively.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Copper-Catalyzed 1,2-Trifluoromethylation Carbonylation of Unactivated Alkenes: Efficient Access to β-Trifluoromethylated Aliphatic Carboxylic Acid Derivatives

Fu-Peng Wu et al.

Summary: A novel copper-catalyzed carbonylative trifluoromethylation of unactivated alkenes has been developed, allowing the preparation of a broad range of beta-trifluoromethylated carboxylic acid derivatives in moderate to excellent yields with excellent regioselectivity. It is worth noting that even the simplest olefin, ethylene gas, can be directly applied to obtain beta-trifluoromethylated amides and esters. This transformation represents the first example of carbonylative trifluoromethylation of alkenes.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Nickel-Catalyzed Multicomponent Coupling: Synthesis of α-Chiral Ketones by Reductive Hydrocarbonylation of Alkenes

Jian Chen et al.

Summary: A nickel-catalyzed, multicomponent regio- and enantioselective coupling method has been developed for synthesizing unsymmetrical dialkyl ketones with a functionalized alpha-stereocenter. This strategy enables the straightforward reductive hydrocarbonylation of a broad range of unactivated alkenes and is suitable for late-stage functionalization of complex molecules.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Multidisciplinary

Copper-Catalyzed Carbonylative Synthesis of β-Boryl Amides via Boroamidation of Alkenes

Fu-Peng Wu et al.

Summary: The study developed a new reaction for synthesizing beta-boryl amides and successfully produced a variety of beta-boryl amides. The research also demonstrated that this method can be used for the transformation of ethylene gas, and achieved enantioselective synthesis. Additionally, the method can directly prepare anticancer drugs.

CCS CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Copper-catalyzed hydroformylation and hydroxymethylation of styrenes

Hui-Qing Geng et al.

Summary: Copper-catalyzed hydroformylation of alkenes has been achieved, leading to the production of aldehydes that can be further hydrogenated to alcohols under the same conditions. The reaction shows excellent regioselectivity and can also be used to synthesize specific compounds by adding alkyl halides.

CHEMICAL SCIENCE (2021)

Article Chemistry, Multidisciplinary

Copper-catalyzed enantioselective carbonylation toward α-chiral secondary amides

Yang Yuan et al.

Summary: This study introduces a copper-catalyzed enantioselective hydroaminocarbonylation method for constructing alpha-chiral secondary amides. The method shows high yields and high levels of enantioselectivity under very mild conditions. Additionally, alpha,beta-Unsaturated secondary amides can be produced by using alkynes as the substrate.

CHEMICAL SCIENCE (2021)

Article Chemistry, Multidisciplinary

Copper-Catalyzed Regioselective Borocarbonylative Coupling of Unactivated Alkenes with Alkyl Halides: Synthesis of β-Boryl Ketones

Fu-Peng Wu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Copper-Catalyzed Carbonylative Hydroamidation of Styrenes to Branched Amides

Yang Yuan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Nickel-Catalyzed Four-Component Carbocarbonylation of Alkenes under 1 atm of CO

Minqi Zhou et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Review Chemistry, Multidisciplinary

First-Row Transition-Metal-Catalyzed Carbonylative Transformations of Carbon Electrophiles

Jin-Bao Peng et al.

CHEMICAL REVIEWS (2019)

Review Biochemistry & Molecular Biology

Natural product syntheses via carbonylative cyclizations

Kaiqing Ma et al.

NATURAL PRODUCT REPORTS (2019)

Article Chemistry, Organic

Nickel-Catalyzed Carbonylation of Difluoroalkyl Bromides with Arylboronic Acids

Hai-Yang Zhao et al.

ORGANIC LETTERS (2019)

Article Chemistry, Physical

A Career in Catalysis: Howard Alper

Dong-Mei Yan et al.

ACS CATALYSIS (2019)

Article Chemistry, Multidisciplinary

A copper-catalyzed carbonylative four-component reaction of ethene and aliphatic olefins

Yahui Li et al.

CHEMICAL COMMUNICATIONS (2018)

Article Chemistry, Multidisciplinary

Synthesis of Allylic Alcohols via Cu-Catalyzed Hydrocarbonylative Coupling of Alkynes with Alkyl Halides

Li-Jie Cheng et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Review Chemistry, Multidisciplinary

Palladium-Catalyzed Carbonylative Multicomponent Reactions

Chaoren Shen et al.

CHEMISTRY-A EUROPEAN JOURNAL (2017)

Article Chemistry, Multidisciplinary

Cu-Catalyzed Hydrocarbonylative C-C Coupling of Terminal Alkynes with Alkyl Iodides

Li-Jie Cheng et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Article Chemistry, Physical

Nanocatalysts for conversion of natural gas to liquid fuels and petrochemical feedstocks

Mahtab Gharibi et al.

APPLIED CATALYSIS A-GENERAL (2012)

Review Chemistry, Multidisciplinary

Recent developments in asymmetric multicomponent reactions

Corien de Graaff et al.

CHEMICAL SOCIETY REVIEWS (2012)

Review Chemistry, Medicinal

Design of Multi-Component Reactions: From libraries of compounds to libraries of reactions

Maxim A. Mironov

QSAR & COMBINATORIAL SCIENCE (2006)

Review Biochemistry & Molecular Biology

The application of multi-component reactions in drug discovery

L Weber

CURRENT MEDICINAL CHEMISTRY (2002)