4.8 Article

N-Allylation of Azoles with Hydrogen Evolution Enabled by Visible- Light Photocatalysis

Related references

Note: Only part of the references are listed.
Review Chemistry, Multidisciplinary

Metallaphotoredox: The Merger of Photoredox and Transition Metal Catalysis

Amy Y. Chan et al.

Summary: The merger of photoredox catalysis with transition metal catalysis, known as metallaphotoredox catalysis, has become an important part of synthetic methodology. It combines the bond formation capability of transition metal catalysis with the utility of photoinduced electron and energy transfer processes. Photocatalytic substrate activation allows the involvement of simple starting materials in metal-mediated bond-forming processes, while electron or energy transfer with organometallic intermediates provides a complementary activation mode to traditional catalytic platforms.

CHEMICAL REVIEWS (2022)

Article Chemistry, Multidisciplinary

General and Efficient C-P Bond Formation by Quantum Dots and Visible Light

Rui-Nan Ci et al.

Summary: This study discovered that semiconductor quantum dots can serve as the sole catalyst to convert H-phosphine oxide into phosphoryl radicals under visible light irradiation, enabling the formation of valuable phosphorus-containing complexes without the use of external oxidants or radical initiators in an atom-economic manner.

CCS CHEMISTRY (2022)

Review Chemistry, Organic

Dual Photoredox and Cobalt Catalysis Enabled Transformations

Kalu Ram Bajya et al.

Summary: Dual photoredox and cobalt catalysis provides a new avenue for transition metal catalyzed cross-coupling reactions. The ability to access low valent cobalt species offers potential for the development of stoichiometric methods.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2022)

Article Multidisciplinary Sciences

Allylic C-H amination cross-coupling furnishes tertiary amines by electrophilic metal catalysis

Siraj Z. Ali et al.

Summary: In this study, a self-regulatory mechanism was developed for allylic carbon-hydrogen amination cross-coupling. By coupling the release of amine nucleophiles with catalyst turnover, excellent regio- and stereoselectivity were achieved. The method successfully produced a variety of drug compounds and complex drug derivatives.

SCIENCE (2022)

Article Chemistry, Multidisciplinary

Cobaloxime Photocatalysis for the Synthesis of Phosphorylated Heteroaromatics

Ji-Xin Yu et al.

Summary: In this study, cobaloxime is used for the first time as a catalyst for the synthesis of phosphorylated heteroaromatics. The catalytic system shows mild conditions, broad substrate scope, and good to excellent yields, indicating great potential for the green synthesis of important organophosphorus chemicals.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Article Chemistry, Physical

Site-selective amination towards tertiary aliphatic allylamines

Shengchun Wang et al.

Summary: The combination of a photocatalyst and cobaloxime enables site-selective amination of olefins with secondary alkyl amines to afford allylic amines. This method is compatible with a broad scope of olefins and can even achieve site- and diastereoselective amination of terpenes.

NATURE CATALYSIS (2022)

Article Chemistry, Organic

Synergistic Organoboron/Palladium Catalysis for Regioselective N-Allylations of Azoles with Allylic Alcohols

Matthew T. Zambri et al.

Summary: A regioselective palladium-catalyzed allylic alkylation method using simple allylic alcohols as electrophile precursors is developed. An organoboron co-catalyst is used to activate the azole-type nucleophile and accelerate the formation of a pi-allylpalladium complex from the allylic alcohol. The method can be applied to various heterocycle types.

ORGANIC LETTERS (2022)

Article Chemistry, Multidisciplinary

Orthogonal Regulation of Nucleophilic and Electrophilic Sites in Pd-Catalyzed Regiodivergent Couplings between Indazoles and Isoprene

Wen-Shuang Jiang et al.

Summary: This study demonstrates an orthogonal regulation of nucleophilic and electrophilic sites in the regiodivergent hydroamination of isoprene with indazoles. By choosing appropriate ligands for electrophilic sites on isoprene and acid co-catalysts for nucleophilic sites on indazoles, different insertion pathways can be controlled. Preliminary experimental studies have been conducted to rationalize the mechanism and regioselectivity, providing insights into the selective functionalization of isoprene and N-functionalization of indazoles.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

4CzIPN-tBu-Catalyzed Proton-Coupled Electron Transfer for Photosynthesis of Phosphorylated N-Heteroaromatics

Yan Liu et al.

Summary: 4,5,6-Tetrakis (3,6-di-tert-butyl-9H-carbazol-9-yl)-isophthalonitrile (4CzIPN-Bu-t) was developed as a photocatalyst for the phosphorus-radical-initiated cascade cyclization reaction of isocyanides. By using 4CzIPN-Bu-t as catalyst, a visible light-induced proton-coupled electron transfer strategy was developed for the generation of phosphorus-centered radicals, leading to the successful construction of phosphorylated phenanthridines, quinolines, and benzothiazoles.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Multidisciplinary

Direct Allylic C(sp3)-H and Vinylic C(sp2)-H Thiolation with Hydrogen Evolution by Quantum Dots and Visible Light

Cheng Huang et al.

Summary: An efficient, atom- and step-economic method for direct allylic C(sp(3))-H thiolation under visible light irradiation is developed in this study, which does not require external oxidants and radical initiators, with hydrogen produced as a byproduct. Radical trapping experiments showed the involvement of allylic radical and thiyl radical in C-S bond formation on the surface of photocatalyst quantum dots.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Quantum dots enable direct alkylation and arylation of allylic C(sp3)-H bonds with hydrogen evolution by solar energy

Cheng Huang et al.

Summary: The study presents a method using semiconductor quantum dots as photocatalysts to directly couple allylic C(sp(3))-H bonds with alpha-amino C-H bonds or heteroarenes under sunlight irradiation. The protocol does not require additional oxidants or reductants, pre-functionalization of coupling partners, and produces hydrogen as a byproduct. This represents the first direct alkylation and arylation of allylic C(sp(3))-H bonds with hydrogen evolution powered by solar energy, showcasing outstanding efficiency, selectivity, step- and atom-economy.
Article Chemistry, Multidisciplinary

Enantioselective Addition of Pyrazoles to Dienes**

Alexander Y. Jiu et al.

Summary: This study presents the first enantioselective addition of pyrazoles to 1,3-dienes, resulting in the formation of secondary and tertiary allylic pyrazoles with excellent regioselectivity. Mechanistic studies indicate a distinct pathway involving Pd-0-catalyzed ligand-to-ligand hydrogen transfer (LLHT), expanding the field of diene hydrofunctionalization with tolerance for various functional groups.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Multidisciplinary Sciences

A cross-dehydrogenative C(sp3)-H heteroarylation via photo-induced catalytic chlorine radical generation

Chia-Yu Huang et al.

Summary: Hydrogen atom abstraction from C(sp(3))-H bonds of naturally abundant alkanes for alkyl radical generation represents a promising yet underexplored strategy in the alkylation reaction designs. The authors demonstrate a photo-induced and chemical oxidant-free cross-dehydrogenative coupling between alkanes and heteroarenes using catalytic chloride and cobalt catalyst, achieving successful couplings with satisfactory yields. The dual catalytic platform features the in situ engendered chlorine radical for alkyl radical generation and exploits the cobaloxime catalyst for catalytic turnover enabling hydrogen evolution.

NATURE COMMUNICATIONS (2021)

Article Chemistry, Multidisciplinary

Homobenzylic Oxygenation Enabled by Dual Organic Photoredox and Cobalt Catalysis

Joshua B. McManus et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Review Chemistry, Multidisciplinary

The Merger of Photoredox and Cobalt Catalysis

Masahiro Kojima et al.

TRENDS IN CHEMISTRY (2020)

Article Chemistry, Organic

Platinum and Gold Catalysis: a la Carte Hydroamination of Terminal Activated Allenes with Azoles

Jose Miguel Alonso et al.

ORGANIC LETTERS (2019)

Article Chemistry, Multidisciplinary

Palladium- and Rhodium-Catalyzed Dynamic Kinetic Resolution of Racemic Internal Allenes Towards Chiral Pyrazoles

Lukas J. Hilpert et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Enantioselective γ-Addition of Pyrazole and Imidazole Heterocycles to Allenoates Catalyzed by Chiral Phosphine

Haiyang Wang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Review Chemistry, Multidisciplinary

Iridium-Catalyzed Asymmetric Allylic Substitution Reactions

Qiang Cheng et al.

CHEMICAL REVIEWS (2019)

Article Chemistry, Multidisciplinary

Palladium-catalyzed N1-selective allylation of indoles with allylic alcohols promoted by titanium tetraisopropoxide

Chieh-Yu Chang et al.

CHEMICAL COMMUNICATIONS (2019)

Review Chemistry, Multidisciplinary

Photocatalytic Activation of Less Reactive Bonds and Their Functionalization via Hydrogen-Evolution Cross-Couplings

Bin Chen et al.

ACCOUNTS OF CHEMICAL RESEARCH (2018)

Article Chemistry, Multidisciplinary

Photocatalytic Dehydrogenative Cross-Coupling of Alkenes with Alcohols or Azoles without External Oxidant

Hong Yi et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

Visible-Light-Mediated Metal-Free Hydrosilylation of Alkenes through Selective Hydrogen Atom Transfer for Si-H Activation

Rong Zhou et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

Acceptorless Dehydrogenation of N-Heterocycles by Merging Visible-Light Photoredox Catalysis and Cobalt Catalysis

Ke-Han He et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

Anti-Markovnikov Oxidation of β-Alkyl Styrenes with H2O as the Terminal Oxidant

Guoting Zhang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Chemistry, Multidisciplinary

Photocatalytic Hydrogen-Evolution Cross-Couplings: Benzene C -H Amination and Hydroxylation

Yi-Wen Zheng et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Multidisciplinary Sciences

Scalable and sustainable electrochemical allylic C-H oxidation

Evan J. Horn et al.

NATURE (2016)

Article Chemistry, Organic

Metal-Free Catalytic Approach for Allylic C-H Amination Using N-Heterocycles via sp3 C-H Bond Activation

Jinwei Sun et al.

JOURNAL OF ORGANIC CHEMISTRY (2015)

Article Chemistry, Multidisciplinary

Atom-Economic, Regiodivergent, and Stereoselective Coupling of Imidazole Derivatives with Terminal Allenes

Kun Xu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Article Chemistry, Multidisciplinary

Mechanistic Insight into the Photoredox Catalysis of Anti-Markovnikov Alkene Hydrofunctionalization Reactions

Nathan A. Romero et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Article Chemistry, Organic

Cross-Coupling Hydrogen Evolution Reaction in Homogeneous Solution without Noble Metals

Jian-Ji Zhong et al.

ORGANIC LETTERS (2014)

Article Chemistry, Multidisciplinary

A Cascade Cross-Coupling Hydrogen Evolution Reaction by Visible Light Catalysis

Qing-Yuan Meng et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

Review Chemistry, Multidisciplinary

Metal-catalyzed enantioselective allylation in asymmetric synthesis

Zhan Lu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2008)

Review Chemistry, Multidisciplinary

Hydroamination:: Direct addition of amines to alkenes and alkynes

Thomas E. Mueller et al.

CHEMICAL REVIEWS (2008)

Review Chemistry, Organic

Recent advances in the chemistry of indazoles

Andreas Schmidt et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2008)

Article Multidisciplinary Sciences

Noxious compounds activate TRPA1 ion channels through covalent modification of cysteines

Lindsey J. Macpherson et al.

NATURE (2007)

Review Chemistry, Multidisciplinary

The growing applications of click chemistry

John E. Moses et al.

CHEMICAL SOCIETY REVIEWS (2007)