One metal two tasks: Reentering the catalytic ending PdII-H for the relay-catalytic cycle for dicarbonylation of amines

Article Chemistry, Multidisciplinary

Photoinduced Acylations Via Azolium-Promoted Intermolecular Hydrogen Atom Transfer

Joshua L. Zhu et al.

Summary: Stable acyl azolium salts can undergo intermolecular HAT reaction upon LED irradiation to afford ketones.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2023)

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Article Chemistry, Organic

Palladium-Catalyzed Regioselective Carbonylation of 2-Trifluoromethyl-1,3-enynes to Multisubstituted Conjugated Dienes

Chang-Sheng Kuai et al.

Summary: A palladium-catalyzed carbonylation of 2-trifluoromethyl-1,3-enynes has been developed, providing access to multisubstituted conjugated dienes. This method exhibits excellent regio- and exclusive (E)-stereoselectivity and demonstrates broad substrate scope with both amines and alcohols as reaction partners, showing promising functional group tolerance.

ORGANIC LETTERS (2023)

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Article Chemistry, Multidisciplinary

Directed Asymmetric Nickel-Catalyzed Reductive 1,2-Diarylation of Electronically Unactivated Alkenes

Zhan Dong et al.

Summary: Transition-metal catalyzed intermolecular 1,2-diarylation of electronically unactivated alkenes is a widely studied topic, but most examples are limited to terminal alkenes. Furthermore, the asymmetric 1,2-diarylation of unactivated alkenes remains unsolved and is challenging. In this study, a highly efficient directed nickel-catalyzed reductive 1,2-diarylation of unactivated internal alkenes with high diastereoselectivities is described. Moreover, enantioselective 1,2-diarylation of unactivated terminal and challenging internal alkenes is achieved with good to high enantioselectivities and high diastereoselectivities by generating a cationic Ni-catalyst through the addition of alkali metal fluoride.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023)

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Article Chemistry, Organic

Palladium-Catalyzed Direct Dicarbonylation of Amines with Ethylene to Imides

Chang-Sheng Kuai et al.

Summary: A palladium-catalyzed method has been developed for the direct and efficient dicarbonylation of amines with ethylene, producing imides with moderate to excellent yields. This method is practical and straightforward, using readily available industrial feedstock.

ORGANIC LETTERS (2022)

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Review Chemistry, Multidisciplinary

Reductive Cross-Coupling of Unreactive Electrophiles

Xiaobo Pang et al.

Summary: Transition-metal-catalyzed reductive coupling of electrophiles is a powerful method for constructing molecules. This review summarizes recent research in our laboratory on this topic, focusing on reactions involving readily available, low-cost, stable but unreactive electrophiles. The findings include deoxygenative C-C coupling of alcohols, reductive alkylation of alkenyl acetates, reductive C-Si coupling of chlorosilanes, and reductive C-Ge coupling of chlorogermanes.

ACCOUNTS OF CHEMICAL RESEARCH (2022)

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Letter Chemistry, Organic

Palladium-Catalyzed Regio- and Stereoselective Hydroaminocarbonylation of Unsymmetrical Internal Alkynes toward α,β-Unsaturated Amides

Chang-Sheng Kuai et al.

Summary: In this study, we reported a method for synthesizing α,β-unsaturated amides via palladium catalysis, which exhibits excellent selectivity and broad adaptability.

ORGANIC LETTERS (2022)

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Review Chemistry, Multidisciplinary

Carboxylic Acids as Adaptive Functional Groups in Metallaphotoredox Catalysis

Sebastian B. Beil et al.

Summary: This article outlines the recent progress in utilizing aliphatic and aromatic carboxylic acids as adaptive functional handles through metallaphotoredox catalysis. Various functionalization reactions can be carried out on these carboxylic acids, providing a powerful tool for drug discovery.

ACCOUNTS OF CHEMICAL RESEARCH (2022)

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Article Chemistry, Multidisciplinary

Nickel-catalyzed alkoxycarbonylation of aryl iodides with 1 atm CO

Ning Liu et al.

Summary: A nickel-catalyzed alkoxycarbonylation reaction of aromatic iodides with alcohols under atmospheric pressure of carbon monoxide is demonstrated. This operationally simple protocol enables the facile synthesis of (hetero)aromatic esters, showing broad substrate scope and excellent functional group tolerance. Various primary and secondary aliphatic alcohols as well as phenols are suitable for this transformation.

CHEMICAL COMMUNICATIONS (2022)

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Article Chemistry, Multidisciplinary

A General and Highly Selective Palladium-Catalyzed Hydroamidation of 1,3-Diynes

Jiawang Liu et al.

Summary: This study describes a new method for chemo-, regio-, and stereoselective mono-hydroamidation of (un)symmetrical 1,3-diynes, utilizing an advanced palladium catalyst system with the ligand Neolephos. The success of this novel transformation is demonstrated by the diversification of several structurally complex molecules and marketed drugs, highlighting the synthetic value of the approach for synthesizing useful α-alkynyl-α, β-unsaturated amides. Control experiments and density-functional theory computations indicate the crucial role of the substrate in controlling the regioselectivity of unsymmetrical 1,3-diynes.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Multidisciplinary

Divergent Aminocarbonylations of Alkynes Enabled by Photoredox/Nickel Dual Catalysis

Xian Zhao et al.

Summary: A metallaphotoredox-catalyzed strategy for the aminocarbonylation of alkynes with amines and CO has been developed. This method allows for selective synthesis of alpha,beta-unsaturated amides and a sequential four-component hydroaminocarbonylation/radical alkylation, demonstrating great potential in the selective and divergent functionalization of alkynes. Preliminary mechanistic studies suggest a photoinduced oxidative insertion of aniline and CO into nickel followed by a migratory insertion of (carbamoyl)nickel species may be involved.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Multidisciplinary

Bimetallic Cooperative Catalysis for Decarbonylative Heteroarylation of Carboxylic Acids via C-O/C-H Coupling

Chengwei Liu et al.

Summary: Cooperative bimetallic catalysis was used in the direct decarbonylative heteroarylation of carboxylic acids, enabling synthesis of important heterobiaryl motifs with high chemoselectivity. This method, which does not require prefunctionalization or directing groups, has a broad substrate scope and shows potential for late-stage modification of pharmaceuticals and streamlined synthesis of bioactive agents. Extensive mechanistic and computational studies were conducted to understand the reaction mechanism, identifying a key step involving the intersection of two catalytic cycles.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Organic

Bimetal Cooperatively Catalyzed Arylalkynylation of Alkynylsilanes

Xing Chen et al.

Summary: An unprecedented Pd/Rh cooperatively catalyzed arylalkynylation of alkynylsilanes was developed to merge an alkynylidene moiety with benzosilacycle, resulting in silaarenes with aggregation-induced emission behavior. Mechanistic investigations revealed that the relay trimetallic transmetalation plays a pivotal role in governing this transformation.

ORGANIC LETTERS (2021)

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Article Chemistry, Organic

Nickel/Photo-Cocatalyzed C(sp2)-H Allylation of Aldehydes and Formamides

Pei Fan et al.

Summary: A nickel/photo-cocatalyzed C(sp(2))-H allylation of aldehydes and formamides is reported in this study, where allyl acetates and allyl alcohols can be used as allylating agents, providing new access to various beta,gamma-unsaturated ketones and amides with high selectivities through the synergistic effect of tetrabutylammonium decatungstate and nickel as catalysts.

ORGANIC LETTERS (2021)

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Review Chemistry, Multidisciplinary

Catalytic three-component dicarbofunctionalization reactions involving radical capture by nickel

Shengqing Zhu et al.

Summary: The merging of nickel catalysis with radical chemistry has provided a new and benign platform for the catalytic dicarbofunctionalization of unsaturated pi bonds with unprecedented reactivity and selectivity. Recent advances in this area mainly involve catalytic domino transformations and exploration of reaction mechanisms.

CHEMICAL SOCIETY REVIEWS (2021)

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Article Chemistry, Organic

Highly regio- and stereoselective synthesis of bis-sulfanyl substituted conjugated dienes by copper-palladium cooperative catalysis

Yuan Li et al.

Summary: The efficient one-pot method for synthesizing symmetric (Z,Z)-isomers of 1,4-bis(sulfanyl)-1,4-diaryl-1,3-butadienes involves the cooperative catalysis of Cu(Xantphos)I and Pd(OAc)(2) along with a base. Preliminary mechanistic studies suggest a double-Sonogashira coupling/double hydrothiolation pathway, with high regio- and stereoselectivity, functional group tolerance, and simplicity of operation.

ORGANIC CHEMISTRY FRONTIERS (2021)

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Review Chemistry, Multidisciplinary

Site-Selective C-H Functionalization via Synergistic Use of Electrochemistry and Transition Metal Catalysis

Ke-Jin Jiao et al.

ACCOUNTS OF CHEMICAL RESEARCH (2020)

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Article Chemistry, Multidisciplinary

Tailored Palladium Catalysts for Selective Synthesis of Conjugated Enynes by Monocarbonylation of 1,3-Diynes

Jiawang Liu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Review Chemistry, Multidisciplinary

Synergistic Dual Transition Metal Catalysis

U. Bin Kim et al.

CHEMICAL REVIEWS (2020)

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Review Chemistry, Multidisciplinary

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

Jin-Bao Peng et al.

CHEMICAL REVIEWS (2019)

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Article Chemistry, Multidisciplinary

Stereoselective Synthesis of Highly Substituted Conjugated Dienes via Pd-Catalyzed Carbonylation of 1,3-Diynes

Jiawang Liu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

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Review Chemistry, Multidisciplinary

Alkyl Carbon-Carbon Bond Formation by Nickel/Photoredox Cross-Coupling

John A. Milligan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

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Review Chemistry, Organic

Hetero-bimetallic cooperative catalysis for the synthesis of heteroarenes

Gaurav R. Gupta et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2019)

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Article Chemistry, Multidisciplinary

Iron-Nickel Dual-Catalysis: A New Engine for Olefin Functionalization and the Formation of Quaternary Centers

Samantha A. Green et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

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Article Chemistry, Multidisciplinary

Mechanistic Interrogation of Co/Ni-Dual Catalyzed Hydroarylation

Sophia L. Shevick et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

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Review Chemistry, Organic

Synergistic Bimetallic Catalysis for Carboboration of Unsaturated Hydrocarbons

Eva Rivera-Chao et al.

SYNTHESIS-STUTTGART (2018)

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Review Chemistry, Multidisciplinary

The merger of transition metal and photocatalysis

Jack Twilton et al.

NATURE REVIEWS CHEMISTRY (2017)

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Article Chemistry, Multidisciplinary

Palladium-catalyzed aminocarbonylation of halo-substituted 7-azaindoles and other heteroarenes using chloroform as a carbon monoxide source

Prakash Kannaboina et al.

CHEMICAL COMMUNICATIONS (2017)

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Review Chemistry, Multidisciplinary

Photochemical Approaches to Complex Chemotypes: Applications in Natural Product Synthesis

Markus D. Karkas et al.

CHEMICAL REVIEWS (2016)

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Editorial Material Chemistry, Organic

Photoredox sheds new light on nickel catalysis: from carbon-carbon to carbon-heteroatom bond formation

Yong-Yuan Gui et al.

ORGANIC CHEMISTRY FRONTIERS (2016)

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Article Chemistry, Multidisciplinary

Carbonylative coupling of allylic acetates with aryl boronic acids

Wei Ma et al.

CHEMICAL COMMUNICATIONS (2015)

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Review Chemistry, Multidisciplinary

Catalytic Silylation of Unactivated C-H Bonds

Chen Cheng et al.

CHEMICAL REVIEWS (2015)

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Review Chemistry, Multidisciplinary

Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds

Alan H. Cherney et al.

CHEMICAL REVIEWS (2015)

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Review Chemistry, Multidisciplinary

Fundamentals of green chemistry: efficiency in reaction design

Roger A. Sheldon

CHEMICAL SOCIETY REVIEWS (2012)

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Review Chemistry, Multidisciplinary

Photochemical Reactions as Key Steps in Natural Product Synthesis

Thorsten Bach et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2011)

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Review Chemistry, Multidisciplinary

Palladium-catalyzed carbonylative coupling reactions between Ar-X and carbon nucleophiles

Xiao-Feng Wu et al.

CHEMICAL SOCIETY REVIEWS (2011)

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Article Chemistry, Multidisciplinary

Palladium-Catalyzed Coupling Reactions: Carbonylative Heck Reactions To Give Chalcones

Xiao-Feng Wu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2010)

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Article Chemistry, Multidisciplinary

Palladium-Catalyzed Carbonylative Heck-Type Reactions of Alkyl Iodides

Kayla S. Bloome et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

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Review Chemistry, Multidisciplinary

Recent Progress in Asymmetric Bifunctional Catalysis Using Multimetallic Systems

Masakatsu Shibasaki et al.

ACCOUNTS OF CHEMICAL RESEARCH (2009)

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Article Chemistry, Multidisciplinary

Palladium-catalyzed oxidative carbonylation of alkyl and aryl indium reagents with CO under mild conditions

Yingsheng Zhao et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)

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Article Chemistry, Multidisciplinary

Heck coupling with nonactivated alkenyl tosylates and phosphates: Examples of effective 1,2-migrations of the alkenyl palladium(II) intermediates

Anders L. Hansen et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2006)

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Article Chemistry, Organic

Regioselective Heck couplings of α,β-unsaturated tosylates and mesylates with electron-rich olefins

AL Hansen et al.

ORGANIC LETTERS (2005)

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Article Chemistry, Organic

Kumada coupling of aryl and vinyl tosylates under mild conditions

ME Limmert et al.

JOURNAL OF ORGANIC CHEMISTRY (2005)

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Article Chemistry, Organic

Fast and regioselective Heck couplings with N-acyl-N-vinylamine derivatives

AL Hansen et al.

JOURNAL OF ORGANIC CHEMISTRY (2005)

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Article Chemistry, Organic

Stereoselective enol tosylation:: Preparation of trisubstituted α,β-unsaturated esters

JM Baxter et al.

ORGANIC LETTERS (2005)

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Article Chemistry, Multidisciplinary

Concise syntheses of meridianins by carbonylative alkynylation and a four-component pyrimidine synthesis

AS Karpov et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2005)

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Article Chemistry, Multidisciplinary

Oxidative addition of aryl tosylates to palladium(0) and coupling of unactivated aryl tosylates at room temperature

AH Roy et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2003)

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Article Chemistry, Multidisciplinary

Efficient palladium-catalyzed coupling of aryl chlorides and tosylates with terminal alkynes: Use of a copper cocatalyst inhibits the reaction

D Gelman et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2003)

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Article Chemistry, Multidisciplinary

Stereoselective synthesis of 2-aminocyclobutanols via photocyclization of α-amido alkylaryl ketones:: Mechanistic implications for the Norrish/Yang reaction

AG Griesbeck et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2002)

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Article Chemistry, Organic

Total synthesis of (±)-cytisine via the intramolecular heck cyclization of activated N-alkyl glutarimides

JW Coe

ORGANIC LETTERS (2000)

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One metal two tasks: Reentering the catalytic ending PdII-H for the relay-catalytic cycle for dicarbonylation of amines

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