4.8 Article

Dual Photoredox and Copper Catalysis: Enantioselective 1,2-Amidocyanation of 1,3-Dienes

Related references

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

Catalytic Asymmetric Hydroalkoxylation and Formal Hydration and Hydroaminoxylation of Conjugated Dienes

Shao-Qian Yang et al.

Summary: In this study, a comprehensive investigation was conducted towards the stereoselective formal hydration and hydroaminoxylation of conjugated dienes by synthesizing new P,N-ligands and identifying an aryl-derived oxime as a surrogate for water and hydroxylamine. Additionally, the asymmetric hydroalkoxylation with new P,N-ligands was elucidated. Furthermore, versatile derivatizations following hydration provided indirect but concise routes to formal hydrophenoxylation, hydrofluoroalkoxylation, and hydrocarboxylation of conjugated dienes that have not been reported before. Finally, a ligand-to-ligand hydrogen transfer process was proposed based on preliminary mechanistic experiments.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2023)

Article Chemistry, Multidisciplinary

Enantioselective Hydroalkoxylation of 1,3-Dienes via Ni-Catalysis

Qi Li et al.

Summary: We report a highly selective addition reaction of alcohols to 1,3-dienes. By using Ni-DuPhos catalyst, enantioenriched allylic ethers can be obtained. The reversibility of C-O bond formation is controlled through solvent-free conditions, and methanol is showcased as a rare reagent in asymmetric synthesis.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2023)

Review Chemistry, Multidisciplinary

Visible Light-Induced Transition Metal Catalysis

Kelvin Pak Shing Cheung et al.

Summary: Visible light-induced transition metal catalysis has emerged as an important development in organic photocatalysis, leading to unprecedented transformations and improvements of known reactions. This method utilizes a single catalytic cycle to harness photon energy, and synergistically combines catalyst-substrate interaction with photoinduced processes.

CHEMICAL REVIEWS (2022)

Review Chemistry, Multidisciplinary

Copper-catalyzed radical relay in C(sp3)-H functionalization

Zuxiao Zhang et al.

Summary: Radical-involved transition metal catalysis enables new reactivities, and copper-catalyzed radical relay shows great potential in C(sp(3))-H functionalization. Significant progress has been made in asymmetric C-H functionalization through ligand design.

CHEMICAL SOCIETY REVIEWS (2022)

Article Chemistry, Multidisciplinary

Photoinduced and palladium-catalyzed hydrogen atom transfer triggered 1,2-difunctionalization of 1,3-dienes with hydroxamides

Xiao-Yun Ruan et al.

Summary: In this study, a photoinduced palladium-catalyzed hydrogen atom transfer triggered 1,2-difunctionalization of conjugated dienes was reported, achieving remote functionalization and selective difunctionalization to synthesize highly diverse amides.

SCIENCE CHINA-CHEMISTRY (2022)

Article Chemistry, Multidisciplinary

Electrophotocatalytic Decoupled Radical Relay Enables Highly Efficient and Enantioselective Benzylic C-H Functionalization

Wenzheng Fan et al.

Summary: A highly efficient and sustainable method for enantioselective benzylic C-H cyanation has been reported by merging electrophoto-and copper catalysis. The novel catalytic system allows independent regulation of key steps to achieve high selectivity, suitable for enantioselective benzylic C-H cyanation of diverse alkylarenes and late-stage functionalization of bioactive molecules.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Article Chemistry, Organic

Redox-Neutral 1,4-Dicarbonfunctionalization of 1,3-Butadiene by Merging Photoredox and Nickel

Du Ding et al.

Summary: In this article, a three-component and redox-neutral synthesis of homoallyl amines and homoallylic alcohols is described. This reaction involves readily available C=X compounds, 1,3-butadiene, and various nucleophiles, and is catalyzed by the combination of photoredox and nickel catalysts.

ORGANIC LETTERS (2022)

Article Chemistry, Multidisciplinary

Photocatalytic Generation of π-allyltitanium Complexes via Radical Intermediates

Fusheng Li et al.

Summary: This study reports a novel photocatalytic strategy for the generation of pi-allyltitanium complexes, allowing for the rapid access to valuable homoallylic alcohols through a three-component allylation reaction with 1,3-butadiene and carbonyls. The exceptional regio- and diastereoselectivity provided by dual photoredox/Ti catalysis is comparable to that of the Cr-catalyzed Nozaki-Hiyama-Kishi allylation reaction.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Palladium-Catalyzed Asymmetric Hydrosulfonylation of 1,3-Dienes with Sulfonyl Hydrazides

Ming-Ming Li et al.

Summary: The highly enantio- and regioselective hydrosulfonylation of 1,3-dienes with sulfonyl hydrazides was achieved using a palladium catalyst containing a monodentate chiral spiro phosphoramidite ligand, providing a practical method for synthesizing chiral allylic sulfones. Mechanistic studies indicated that the reaction proceeds through the formation of an allyl hydrazine intermediate and subsequent rearrangement to the chiral allylic sulfone product, with the enantioselectivity determined in the conversion from the intermediate to the product.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Visible-Light-Induced 1,3-Aminopyridylation of [1.1.1]Propellane with N-Aminopyridinium Salts

Sanghoon Shin et al.

Summary: The formation of an electron donor-acceptor complex allowed for the direct installation of amino and pyridyl groups onto bicyclo[1.1.1]pentane (BCP) frameworks in the absence of an external photocatalyst. This method is robust and metal-free, enabling late-stage modification of structurally complex biorelevant molecules. The strategy also facilitates the incorporation of functional groups with pyridine across the BCP core, significantly expanding the range of potential applications for drug discovery.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Selective 1,2-Aminoisothiocyanation of 1,3-Dienes Under Visible-Light Photoredox Catalysis

Weisi Guo et al.

Summary: This study reports a highly chemo- and regio-selective 1,2-aminoisothiocyanation reaction of 1,3-dienes using N-aminopyridinium salts and TMSNCS under mild photoredox catalytic conditions. The selective formation of products is attributed to the facile isomerization of allyl thiocyanates to allyl isothiocyanates under photocatalytic conditions, offering potential applications in the synthesis of allyl isothiocyanates.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Enantioselective Radical Carbocyanation of 1,3-Dienes via Photocatalytic Generation of Allylcopper Complexes

Fu-Dong Lu et al.

Summary: By synergetic photoredox/copper catalysis, enantioselective carbocyanation of 1,3-dienes can be achieved with high efficiency and selectivity, and the method shows good potential for expansion to other substrates such as 1,3-enynes.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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 Chemistry, Multidisciplinary

Photoinduced Copper-Catalyzed Asymmetric Three-Component Coupling of 1,3-Dienes: An Alternative to Kharasch-Sosnovsky Reaction

Peng-Zi Wang et al.

Summary: A new method for three-component coupling reaction using chiral copper catalyst and purple-LED irradiation as an alternative to allylic oxidation was reported. The reaction features mild conditions, broad scope, and high functional group tolerance, making it useful for late-stage modification of pharmaceuticals and natural products. Detailed mechanistic studies support a radical-based reaction pathway.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Photoinduced Copper-Catalyzed Asymmetric C-O Cross-Coupling

Jun Chen et al.

Summary: This study presents a photoinduced copper-catalyzed cross-coupling reaction for the generation of allylic esters. The reaction proceeds at room temperature with high regio- and enantioselectivity.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Physical

Photoredox Catalytic Three-Component Amidoazidation of 1,3-Dienes

Dan Forster et al.

Summary: Despite the potential for the synthesis of functionalized allylic azides, only limited synthetic routes have been developed. A three-component 1,2-amidoazidation of 1,3-dienes has been reported, showing high efficiency in producing 1,2-amidoazidation products. Reduction of the mixture significantly enriches one of the isomers, thanks to the facile 1,3-azide shift of the allyl azides under dynamic kinetic conditions.

ACS CATALYSIS (2021)

Review Chemistry, Multidisciplinary

Visible light photoredox-catalysed remote C-H functionalisation enabled by 1,5-hydrogen atom transfer (1,5-HAT)

Weisi Guo et al.

Summary: This tutorial review summarizes the recent progress in remote functionalization of C-H bonds, with a focus on photoredox-catalyzed remote C-H functionalization.

CHEMICAL SOCIETY REVIEWS (2021)

Review Chemistry, Multidisciplinary

Pyridinium Salts as Redox-Active Functional Group Transfer Reagents

Simon L. Roessler et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Photoinduced Palladium-Catalyzed Carbofunctionalization of Conjugated Dienes Proceeding via Radical-Polar Crossover Scenario: 1,2-Aminoalkylation and Beyond

Kelvin Pak Shing Cheung et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Multidisciplinary

Three-Component, Interrupted Radical Heck/Allylic Substitution Cascade Involving Unactivated Alkyl Bromides

Huan-Ming Huang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Physical

Catalytic radical generation of π-allylpalladium complexes

Huan-Ming Huang et al.

NATURE CATALYSIS (2020)

Article Chemistry, Multidisciplinary

Visible-Light-Enabled Ortho-Selective Aminopyridylation of Alkenes with N-Aminopyridinium Ylides

Yonghoon Moon et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Multidisciplinary Sciences

Copper-catalyzed remote C(sp3)-H azidation and oxidative trifluoromethylation of benzohydrazides

Xu Bao et al.

NATURE COMMUNICATIONS (2019)

Article Chemistry, Multidisciplinary

Remote C(sp3)-H Arylation and Vinylation of N-Alkoxypyridinium Salts to δ-Aryl and δ-Vinyl Alcohols

Xu Bao et al.

CHEMISTRY-A EUROPEAN JOURNAL (2019)

Review Chemistry, Physical

Recent Advances in Pyridinium Salts as Radical Reservoirs in Organic Synthesis

Fu-Sheng He et al.

ACS CATALYSIS (2019)

Article Chemistry, Organic

Visible-Light-Mediated Amination of π-Nucleophiles with N-Aminopyridinium Salts

Katarzyna Goliszewska et al.

JOURNAL OF ORGANIC CHEMISTRY (2019)

Article Chemistry, Organic

Ni-Catalyzed Regioselective Hydroalkoxylation of Branched 1,3-Dienes

Gael Tran et al.

ORGANIC LETTERS (2019)

Article Multidisciplinary Sciences

Visible light induced alkene aminopyridylation using N-aminopyridinium salts as bifunctional reagents

Yonghoon Moon et al.

NATURE COMMUNICATIONS (2019)

Article Chemistry, Multidisciplinary

Palladium-Catalyzed Asymmetric Aminohydroxylation of 1,3-Dienes

Hong-Cheng Shen et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Enantioselective 1,2-Difunctionalization of 1,3-Butadiene by Sequential Alkylation and Carbonyl Allylation

Yang Xiong et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Chemistry, Organic

Regiospecific Three-Component Aminofluorination of Olefins via Photoredox Catalysis

Jia-Nan Mo et al.

ORGANIC LETTERS (2018)

Article Chemistry, Organic

Recent advances on catalytic asymmetric difunctionalization of 1,3-dienes

Yang Xiong et al.

TETRAHEDRON LETTERS (2018)

Review Chemistry, Multidisciplinary

Copper-Catalyzed Radical Relay for Asymmetric Radical Transformations

Fei Wang et al.

ACCOUNTS OF CHEMICAL RESEARCH (2018)

Article Chemistry, Multidisciplinary

Copper-Catalyzed Arylation of Remote C(sp(3))-H Bonds in Carboxamides and Sulfonamides

Zhaodong Li et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Enantioselective Intermolecular Addition of Aliphatic Amines to Acyclic Dienes with a Pd-PHOX Catalyst

Nathan J. Adamson et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Article Chemistry, Multidisciplinary

Rhodium-Catalyzed Hydrofunctionalization: Enantioselective Coupling of Indolines and 1,3-Dienes

Xiao-Hui Yang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Article Chemistry, Multidisciplinary

Chiral Pincer Carbodicarbene Ligands for Enantioselective Rhodium-Catalyzed Hydroarylation of Terminal and Internal 1,3-Dienes with Indoles

Justin S. Marcum et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Article Chemistry, Multidisciplinary

Enantioselective Decarboxylative Cyanation Employing Cooperative Photoredox Catalysis and Copper Catalysis

Dinghai Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Review Chemistry, Multidisciplinary

The merger of transition metal and photocatalysis

Jack Twilton et al.

NATURE REVIEWS CHEMISTRY (2017)

Article Chemistry, Multidisciplinary

Highly Diastereo- and Enantioselective Cu-Catalyzed Borylative Coupling of 1,3-Dienes and Aldimines

Liyin Jiang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Multidisciplinary

Catalytic Enantioselective Assembly of Homoallylic Alcohols from Dienes, Aryldiazonium Salts, and Aldehydes

Zhong-Lin Tao et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Review Chemistry, Multidisciplinary

Dual Catalysis Strategies in Photochemical Synthesis

Kazimer L. Skubi et al.

CHEMICAL REVIEWS (2016)

Article Chemistry, Multidisciplinary

Iron(II)-Catalyzed Intermolecular Aminofluorination of Unfunctionalized Olefins Using Fluoride Ion

Deng-Fu Lu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Chemistry, Multidisciplinary

Enantioselective Copper-Catalyzed Intermolecular Cyanotrifluoromethylation of Alkenes via Radical Process

Fei Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Multidisciplinary Sciences

Enantioselective cyanation of benzylic C-H bonds via copper-catalyzed radical relay

Wen Zhang et al.

SCIENCE (2016)

Article Chemistry, Multidisciplinary

Regiospecific Intermolecular Aminohydroxylation of Olefins by Photoredox Catalysis

Kazuki Miyazawa et al.

CHEMISTRY-A EUROPEAN JOURNAL (2015)

Review Chemistry, Organic

The Diels-Alder Reaction in Steroid Synthesis

Emily G. Mackay et al.

SYNTHESIS-STUTTGART (2015)

Review Chemistry, Multidisciplinary

Catalytic Diamination of Olefins via N-N Bond Activation

Yingguang Zhu et al.

ACCOUNTS OF CHEMICAL RESEARCH (2014)

Article Chemistry, Multidisciplinary

The Asymmetric Hetero-Diels-Alder Reaction in the Syntheses of Biologically Relevant Compounds

Vincent Eschenbrenner-Lux et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Review Chemistry, Multidisciplinary

Catalytic bismetallative multicomponent coupling reactions: scope, applications, and mechanisms

Hee Yeon Cho et al.

CHEMICAL SOCIETY REVIEWS (2014)

Article Chemistry, Medicinal

Peptides Containing β-Amino Acid Patterns: Challenges and Successes in Medicinal Chemistry

Chiara Cabrele et al.

JOURNAL OF MEDICINAL CHEMISTRY (2014)

Article Chemistry, Multidisciplinary

Iridium-Catalyzed Annulation of Salicylimines with 1,3-Dienes

Yusuke Ebe et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Article Chemistry, Multidisciplinary

Catalytic Enantioselective 1,2-Diboration of 1,3-Dienes: Versatile Reagents for Stereoselective Allylation

Laura T. Kliman et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

Article Chemistry, Multidisciplinary

Iron Catalyzed Asymmetric Oxyamination of Olefins

Kevin S. Williamson et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

Article Chemistry, Multidisciplinary

Nickel-Catalyzed Asymmetric Addition of Alkyne C-H Bonds across 1,3-Dienes Using Taddol-Based Chiral Phosphoramidite Ligands

Masamichi Shirakura et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2010)

Review Chemistry, Multidisciplinary

Recent advances in the catalytic asymmetric synthesis of beta-amino acids

Barbara Weiner et al.

CHEMICAL SOCIETY REVIEWS (2010)

Review Chemistry, Organic

Enantioselective Preparation of β2-Amino Acid Derivatives for β-Peptide Synthesis

Dieter Seebach et al.

SYNTHESIS-STUTTGART (2009)

Review Chemistry, Multidisciplinary

β-peptides:: From structure to function

RP Cheng et al.

CHEMICAL REVIEWS (2001)