Photoredox/Nickel-Catalyzed Single-Electron Tsuji-Trost Reaction: Development and Mechanistic Insights. Academic Article

abstract

• A regioselective, nickel-catalyzed photoredox allylation of secondary, benzyl, and -alkoxy radical precursors is disclosed. Through this manifold, a variety of linear allylic alcohols and allylated monosaccharides are accessible in high yields under mild reaction conditions. Quantum mechanical calculations [DFT and DLPNO-CCSD(T)] support the mechanistic hypothesis of a Ni0 to NiII oxidative addition pathway followed by radical addition and inner-sphere allylation.

authors

• Gutierrez Santacruz, Osvaldo

published proceedings

• Angew Chem Int Ed Engl

altmetric score

• 6.05

author list (cited authors)

• Matsui, J. K., Gutirrez-Bonet, . ., Rotella, M., Alam, R., Gutierrez, O., & Molander, G. A.

citation count

• 77

complete list of authors

• Matsui, Jennifer K||Gutiérrez-Bonet, Álvaro||Rotella, Madeline||Alam, Rauful||Gutierrez, Osvaldo||Molander, Gary A

publication date

• January 2018

publisher

• Wiley  Publisher

published in

• Angewandte Chemie International Edition  Journal

keywords

• Allylic Compounds
• Catalysis
• Electrons
• Molecular Structure
• Nickel
• Oxidation-Reduction
• Photochemical Processes
• Photochemistry
• Propanols
• Quantum Theory
• Reaction Mechanisms
• Synthetic Methods

PubMed Central ID

• 30307672

Digital Object Identifier (DOI)

• 10.1002/anie.201809919

start page

• 15847

end page

• 15851

volume

• 57

issue

• 48

URL

• http://dx.doi.org/10.1002/anie.201809919