Ni-Catalyzed enantioselective reductive arylcyanation/cyclization of N-(2-iodo-aryl) acrylamide

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)

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Article Chemistry, Multidisciplinary

Enantioselective Synthesis of α-All-Carbon Quaternary Center-Containing Carbazolones via Amino-palladation/Desymmetrizing Nitrile Addition Cascade

Xu-Dong Hu et al.

Summary: This research presents an efficient enantioselective Pd(II)-catalyzed cascade reaction for the transformation of alkyne-tethered malononitriles into alpha-quaternary carbazolones with high enantioselectivities. The utility of this method is demonstrated by the synthesis of diverse heterocycles and a nitrile-containing leucomidine A analog from the obtained products.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Article Chemistry, Multidisciplinary

Ni-catalyzed enantioselective [2+2+2] cycloaddition of malononitriles with alkynes

Jinhui Cai et al.

Summary: This study presents an efficient strategy for assembling enantioenriched pyridine derivatives by forming three bonds and one quaternary stereocenter simultaneously in a single reaction step. The reaction utilizes bio-renewable 2-MeTHF as the solvent, features mild reaction conditions, and shows good functional group compatibilities and enantioselectivities.

CHEM (2021)

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Article Chemistry, Multidisciplinary

Nickel-Catalyzed Asymmetric Reductive Carbo-Carboxylation of Alkenes with CO2

Xiao-Wang Chen et al.

Summary: The asymmetric reductive carbo-carboxylation of alkenes via nickel catalysis provides an efficient method for the synthesis of carboxylic acids with mild reaction conditions, wide substrate scope, and good selectivity. This approach opens up a new avenue for the total synthesis of chiral natural products using CO2.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Organic

Access to α-Cyano Carbonyls Bearing a Quaternary Carbon Center by Reductive Cyanation

Xinyi Ren et al.

Summary: A method for reductive cyanation of tertiary alkyl bromides was developed, providing good to excellent yields of various alpha-cyano ketones, esters, and carboxamides containing a nitrile-bearing all-carbon quaternary center under mild reaction conditions. The corresponding reaction mechanism involving in situ generated organozinc reagent and reactivity distinction was elucidated by density functional theory computation.

ORGANIC LETTERS (2021)

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Article Chemistry, Multidisciplinary

Design of an Electron-Withdrawing Benzonitrile Ligand for Ni-Catalyzed Cross-Coupling Involving Tertiary Nucleophiles

L. Reginald Mills et al.

Summary: New ligands are designed to exploit the reactivity of nitrile-containing additives in Ni catalysis for cross-coupling reactions involving tertiary nucleophiles. Kinetic and Hammett studies elucidate the role of the optimized ligand, promoting reductive elimination and stabilizing low-valent Ni. This study enables the synthesis of quaternary alpha-arylnitriles from disubstituted malononitriles through decyanation-metalation and Ni-catalyzed arylation.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Article Chemistry, Organic

Synthesis of 3,3-Dialkyl-Substituted Isoindolinones Enabled by Nickel-Catalyzed Reductive Dicarbofunctionalization of Enamides

Ke Fang et al.

Summary: A novel nickel-catalyzed reaction method for the synthesis of 3,3-dialkyl-substituted isoindolinone frameworks from unactivated alkyl iodides and 1,1-disubstituted enamides has been reported. The method exhibits good functional group tolerance and enantioselectivity through the use of commercially available chiral Bn-Biox ligand.

ORGANIC LETTERS (2021)

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Article Chemistry, Organic

Ni-Catalyzed Reductive Arylcyanation of Alkenes

Hengxu Li et al.

Summary: A Ni-catalyzed reductive arylcyanation of alkene using an environmentally benign and nontoxic organo cyanating reagent has been developed. This method allows for the rapid synthesis of cyanosubstituted oxindoles and isoquinoline-1,3-diones with high functional group tolerance, and also features an enantioselective version for the construction of enantiomerically enriched 3-cyanomethyl oxindoles. Additionally, this approach has been successfully applied to the synthesis of natural alkaloids (+)-esermethole and (+)-physostigmine.

ORGANIC LETTERS (2021)

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Article Chemistry, Multidisciplinary

Access to 1,3-Dinitriles by Enantioselective Auto-tandem Catalysis: Merging Allylic Cyanation with Asymmetric Hydrocyanation

Jinguo Long et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Article Chemistry, Multidisciplinary

Enantioselective Assembly of Cycloenones with a Nitrile-Containing All-Carbon Quaternary Center from Malononitriles Enabled by Ni Catalysis

Zhiwu Lu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Article Chemistry, Organic

Nickel-Catalyzed Asymmetric Reductive Arylbenzylation of Unactivated Alkenes

Youxiang Jin et al.

ORGANIC LETTERS (2020)

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Article Chemistry, Multidisciplinary

Dual electrocatalysis enables enantioselective hydrocyanation of conjugated alkenes

Lu Song et al.

NATURE CHEMISTRY (2020)

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Article Chemistry, Physical

Catalytic Enantioselective Cyanation: Recent Advances and Perspectives

Wen-Biao Wu et al.

ACS CATALYSIS (2020)

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Article Chemistry, Physical

Nickel-Catalyzed Enantioselective Reductive Cross-Coupling Reactions

Kelsey E. Poremba et al.

ACS CATALYSIS (2020)

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Article Chemistry, Physical

Nickel-Catalyzed Dicarbofunctionalization of Alkenes

Xiaoxu Qi et al.

ACS CATALYSIS (2020)

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Article Chemistry, Multidisciplinary

Quinim: A New Ligand Scaffold Enables Nickel-Catalyzed Enantioselective Synthesis of α-Alkylated γ-Lactam

Xianqing Wu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Review Chemistry, Organic

SYNTHESIS OF NITROGEN HETEROCYCLES THROUGH CYANATIVE CYCLIZATION AND CYCLOADDITION REACTIONS UNDER TRANSITION METAL CATALYSIS

Shigeru Arai et al.

HETEROCYCLES (2020)

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Review Chemistry, Organic

Recent progress in transition-metal-catalyzed hydrocyanation of nonpolar alkenes and alkynes

Hongru Zhang et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2020)

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Article Chemistry, Multidisciplinary

Nickel-Catalyzed Asymmetric Reductive Arylalkylation of Unactivated Alkenes

Youxiang Jin et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

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Article Chemistry, Multidisciplinary

Asymmetric Propargylic Radical Cyanation Enabled by Dual Organophotoredox and Copper Catalysis

Fu-Dong Lu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

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Article Chemistry, Multidisciplinary

Highly Enantioselective Cross-Electrophile Aryl-Alkenylation of Unactivated Alkenes

Zhi-Xiong Tian et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

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Article Chemistry, Physical

Enantioselective and Regioselective Copper-Catalyzed Borocyanation of 1-Aryl-1,3-Butadienes

Tao Jia et al.

ACS CATALYSIS (2019)

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Article Chemistry, Multidisciplinary

New Bisoxazoline Ligands Enable Enantioselective Electrocatalytic Cyanofunctionalization of Vinylarenes

Niankai Fu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

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Article Chemistry, Multidisciplinary

Ni-Catalyzed Reductive Cyanation of Aryl Halides and Phenol Derivatives via Transnitrilation

L. Reginald Mills et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

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Article Multidisciplinary Sciences

Site-specific allylic C-H bond functionalization with a copper-bound N-centred radical

Jiayuan Li et al.

NATURE (2019)

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Article Chemistry, Multidisciplinary

Chiral Piperidines from Acyclic Amines via Enantioselective, Radical-Mediated δ C-H Cyanation

Zuxiao Zhang et al.

CHEM (2019)

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Article Chemistry, Organic

Nickel-Catalyzed Intramolecular Arylcyanation for the Synthesis of 3,3-Disubstituted Oxindoles

Andy Yen et al.

ORGANIC LETTERS (2018)

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Article Chemistry, Physical

Merging Photoredox and Copper Catalysis: Enantioselective Radical Cyanoalkylation of Styrenes

Wanxing Sha et al.

ACS CATALYSIS (2018)

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Article Chemistry, Multidisciplinary

Ni-Catalyzed Enantioselective Reductive Diarylation of Activated Alkenes by Domino Cyclization/Cross-Coupling

Kuai Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

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Article Chemistry, Multidisciplinary

Enantioselective Decarboxylative Cyanation Employing Cooperative Photoredox Catalysis and Copper Catalysis

Dinghai Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

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Article Chemistry, Organic

Enantioselective Nickel-Catalyzed Mizoroki Heck Cyclizations To Generate Quaternary Stereocenters

Jean-Nicolas Desrosiers et al.

ORGANIC LETTERS (2017)

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Article Chemistry, Multidisciplinary

Enantioselective Copper-Catalyzed Intermolecular Cyanotrifluoromethylation of Alkenes via Radical Process

Fei Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

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Article Multidisciplinary Sciences

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

Wen Zhang et al.

SCIENCE (2016)

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Article Chemistry, Medicinal

Nitrile-Containing Pharmaceuticals: Efficacious Roles of the Nitrile Pharmacophore

Fraser F. Fleming et al.

JOURNAL OF MEDICINAL CHEMISTRY (2010)

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Article Chemistry, Multidisciplinary

Asymmetric intramolecular arylcyanation of unactivated Olefins via C-CN bond activation

Mary P. Watson et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)

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Article Chemistry, Multidisciplinary

Intramolecular arylcyanation of alkenes catalyzed by nickel/AlMe2CI

Yoshiaki Nakao et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)

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Article Chemistry, Multidisciplinary

Why excess cyanide can be detrimental to Pd-catalyzed cyanation of haloarenes.: Facile formation and characterization of [Pd(CN)3(H)]2- and [Pd(CN)3(Ph)]2-

Kerwin D. Dobbs et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2007)

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Article Chemistry, Multidisciplinary

Palladium-catalyzed enantioselective domino Heck-cyanation sequence: Development and application to the total synthesis of esermethole and physostigmine

Artur Pinto et al.

CHEMISTRY-A EUROPEAN JOURNAL (2007)

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Ni-Catalyzed enantioselective reductive arylcyanation/cyclization of N-(2-iodo-aryl) acrylamide

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