Oxidative Addition of Water, Alcohols, and Amines in Palladium Catalysis
Grünwald A, Heinemann FW, Munz D (2020)
Publication Type: Journal article
Publication year: 2020
Journal
Abstract
The homolytic cleavage of O-H and N-H or weak C-H bonds is a key elementary step in redox catalysis, but is thought to be unfeasible for palladium. In stark contrast, reported here is the room temperature and reversible oxidative addition of water, isopropanol, hexafluoroisopropanol, phenol, and aniline to a palladium(0) complex with a cyclic (alkyl)(amino)carbene (CAAC) and a labile pyridino ligand, as is also the case in popular N-heterocyclic carbene (NHC) palladium(II) precatalysts. The oxidative addition of protic solvents or adventitious water switches the chemoselectivity in catalysis with alkynes through activation of the terminal C-H bond. Most salient, the homolytic activation of alcohols and amines allows atom-efficient, additive-free cross-coupling and transfer hydrogenation under mild reaction conditions with usually unreactive, yet desirable reagents, including esters and bis(pinacolato)diboron.
Authors with CRIS profile
Annette Grünwald
Lehrstuhl für Anorganische und Allgemeine Chemie
Frank Wilhelm Heinemann
Lehrstuhl für Anorganische und Allgemeine Chemie
Involved external institutions
Germany (DE)How to cite
APA:
Grünwald, A., Heinemann, F.W., & Munz, D. (2020). Oxidative Addition of Water, Alcohols, and Amines in Palladium Catalysis. Angewandte Chemie International Edition. https://doi.org/10.1002/anie.202008350
MLA:
Grünwald, Annette, Frank Wilhelm Heinemann, and Dominik Munz. "Oxidative Addition of Water, Alcohols, and Amines in Palladium Catalysis." Angewandte Chemie International Edition (2020).
BibTeX: Download