SCHOLARLY PUBLICATION ✓ Open Access

Practical Ni-Catalyzed Aryl–Alkyl Cross-Coupling of Secondary Redox-Active Esters

Josep Cornellà, Jacob T. Edwards, Tian Qin, Shuhei Kawamura, Jie Wang, Chung‐Mao Pan, Ryan Gianatassio, Michael A. Schmidt, Martin D. Eastgate, Phil S. Baran

📖 Journal of the American Chemical Society → 📅 2016-02-02 🔗 DOI: 10.1021/jacs.6b00250

View Journal Profile → ⬇ Download PDF View Official Paper ↗

📄 Abstract

A new transformation is presented that enables chemists to couple simple alkyl carboxylic acids with aryl zinc reagents under Ni-catalysis. The success of this reaction hinges on the unique use of redox-active esters that allow one to employ such derivatives as alkyl halides surrogates. The chemistry exhibits broad substrate scope and features a high degree of practicality. The simple procedure and extremely inexpensive nature of both the substrates and pre-catalyst (NiCl2·6H2O, ca. $9.5/mol) bode well for the immediate widespread adoption of this method.

📄 Abstract

📤 Share this page

🔬 Related Research Papers

Microfluidic Fabrication of Monodisperse Biocompatible and Biodegradable Polymersomes with Controlled Permeability

A Perfectly Hydrophobic Surface (θ A /θ R = 180°/180°)

Fine-Tuned Photoactive and Interconnection Layers for Achieving over 13% Efficiency in a Fullerene-Free Tandem Organic Solar Cell

A Versatile Kinetics-Controlled Coating Method To Construct Uniform Porous TiO2 Shells for Multifunctional Core–Shell Structures

Direct In situ Observation of Li2O Evolution on Li-Rich High-Capacity Cathode Material, Li[NixLi(1–2x)/3Mn(2–x)/3]O2 (0 ≤ x ≤0.5)

Ex Situ Generation of Stoichiometric and Substoichiometric 12CO and 13CO and Its Efficient Incorporation in Palladium Catalyzed Aminocarbonylations

Serial Ligand Catalysis: A Highly Selective Allylic C−H Oxidation

Processing Pathway Dependence of Amorphous Silica Nanoparticle Toxicity: Colloidal vs Pyrolytic

Highly Enantioselective Direct Conjugate Addition of Ketones to Nitroalkenes Promoted by A Chiral Primary Amine−Thiourea Catalyst

Hydrogen Storage in a Prototypical Zeolitic Imidazolate Framework-8

Grain-Boundary-Rich Copper for Efficient Solar-Driven Electrochemical CO 2 Reduction to Ethylene and Ethanol

Acid-Resistant Mesoporous Metal–Organic Framework toward Oral Insulin Delivery: Protein Encapsulation, Protection, and Release