Borates as a Traceless Activation Group for Intermolecular Alkylarylation of Ethylene through Photoredox/Nickel Dual Catalysis

We report a full account of our research on nickel-catalyzed Markovnikov-selective hydroarylation and hydroalkenylation of non-conjugated alkenes, which has yielded a toolkit of methods that proceed under mild conditions with alkenyl sulfonamide, ketone, and amide substrates. Regioselectivity is controlled through catalyst coordination to the native Lewis basic functional groups contained within these substrates. To maximize product yield, reaction conditions were fine-tuned for each substrate class, reflecting the different coordination properties of the directing functionality. Detailed kinetic and computational studies shed light on the mechanism of this family of transformations, pointing to transmetalation as the turnover-limiting step.

Download Full-text

Coupling reaction of Aryl Halides Promoted by NiCl2/PPh3/Sm0

Journal of Chemical Research ◽

10.3184/030823402103170772 ◽

2002 ◽

Vol 2002 (11) ◽

pp. 562-563 ◽

Cited By ~ 5

Author(s):

Xingliang Zheng ◽

Yongmin Zhang

Keyword(s):

Functional Groups ◽

Coupling Reaction ◽

Aryl Halides ◽

Efficient Synthesis ◽

Mild Conditions ◽

Coupling Reagent ◽

High Yields

An efficient synthesis of biaryls from various aryl halides has been developed and investigated. The coupling reagent is a catalytic mixture of anhydrous NiCl2 and PPh3 in the presence of metallic samarium. The reaction occurs rapidly under mild conditions, tolerates a variety of functional groups with high yields.

Download Full-text

Directed Markovnikov Hydroarylation and Hydroalkenylation of Alkenes Under Nickel Catalysis

10.26434/chemrxiv.14639778 ◽

2021 ◽

Author(s):

Zi-Qi Li ◽

Omar Apolinar ◽

Ruohan Deng ◽

Keary Engle

Keyword(s):

Functional Groups ◽

Product Yield ◽

Computational Studies ◽

Nickel Catalysis ◽

Reaction Conditions ◽

Full Account ◽

Coordination Properties ◽

Mild Conditions ◽

Limiting Step ◽

Shed Light

We report a full account of our research on nickel-catalyzed Markovnikov-selective hydroarylation and hydroalkenylation of non-conjugated alkenes, which has yielded a toolkit of methods that proceed under mild conditions with alkenyl sulfonamide, ketone, and amide substrates. Regioselectivity is controlled through catalyst coordination to the native Lewis basic functional groups contained within these substrates. To maximize product yield, reaction conditions were fine-tuned for each substrate class, reflecting the different coordination properties of the directing functionality. Detailed kinetic and computational studies shed light on the mechanism of this family of transformations, pointing to transmetalation as the turnover-limiting step.

Download Full-text

Faculty Opinions recommendation of Dual catalysis. Merging photoredox with nickel catalysis: coupling of α-carboxyl sp³-carbons with aryl halides.

Faculty Opinions – Post-Publication Peer Review of the Biomedical Literature ◽

10.3410/f.718437315.793499306 ◽

2014 ◽

Author(s):

Miles Congreve ◽

Mark Pickworth

Keyword(s):

Aryl Halides ◽

Nickel Catalysis ◽

Dual Catalysis

Download Full-text

Faculty Opinions recommendation of Dual catalysis. Merging photoredox with nickel catalysis: coupling of α-carboxyl sp³-carbons with aryl halides.

Faculty Opinions – Post-Publication Peer Review of the Biomedical Literature ◽

10.3410/f.718437315.793496159 ◽

2014 ◽

Author(s):

Robert Garbaccio

Keyword(s):

Aryl Halides ◽

Nickel Catalysis ◽

Dual Catalysis

Download Full-text

Carbon-Heteroatom Cross-Coupling via an Electronically Excited Nickel (II) Complex

10.26434/chemrxiv.9736049.v1 ◽

2019 ◽

Author(s):

Randolph Escobar ◽

Jeffrey Johannes

Keyword(s):

Energy Transfer ◽

Functional Groups ◽

Cross Coupling ◽

Reductive Elimination ◽

Aryl Halides ◽

Coupling Reactions ◽

General Methodology ◽

Cross Coupling Reactions ◽

Electronically Excited ◽

Energy Transfer Pathway

<div>While carbon-heteroatom cross coupling reactions have been extensively studied, many methods are specific and</div><div>limited to a set of substrates or functional groups. Reported here is a method that allows for C-O, C-N and C-S cross coupling reactions under one general methodology. We propose that an energy transfer pathway, in which an iridium photosensitizer produces an excited nickel (II) complex, is responsible for the key reductive elimination step that couples aryl halides to 1° and 2° alcohols, anilines, thiophenols, carbamates and sulfonamides.</div>

Download Full-text

Chiral Mn(III) Salen Complex Immobilized on CuFe2O4@SiO2-NH2 NPs: A Cheap and Efficient Catalyst for N-arylation of Aryl Halides and Phenylboronic Acid Under Mild Conditions

Letters in Organic Chemistry ◽

10.2174/1570178616666190919110639 ◽

2020 ◽

Vol 17 (11) ◽

pp. 857-863

Author(s):

Mohammad Ali Nasseri ◽

Seyyedeh Ameneh Alavi ◽

Milad Kazemnejadi ◽

Ali Allahresani

Keyword(s):

Phenylboronic Acid ◽

Significant Loss ◽

Aryl Halides ◽

Coupling Reactions ◽

Efficient Catalyst ◽

Aryl Chlorides ◽

Mild Conditions ◽

Cross Coupling Reactions ◽

Salen Complex ◽

Ft Ir

A convenient and efficient chiral CuFe2O4@SiO2-Mn(III) Ch.salen nanocatalyst has been developed for the C-N cross-coupling reactions of aryl halides/ phenylboronic acid with N-heterocyclic compounds in water and/or DMSO under mild conditions. The catalyst could be applied for the N-arylation of a variety of nitrogen-containing heterocycles with aryl chlorides, bromides, iodides and phenylboronic acid under mild conditions. Moderate to good yields were achieved for all substrates. The structure of catalyst was characterized using various techniques including FT-IR, FE-SEM, EDX, XRD, TEM and TGA. The catalyst can be simply recovered and reused for several times without significant loss of activity.

Download Full-text