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6H-Dibenzo[d,f-[1,3]diazepin-6-ylidene,5,7-dihydro-5,7-diphenylphosphanyl]: A new ligand for palladium-catalyzed Mizoroki–Heck coupling

Paper ID Volume ID Publish Year Pages File Format Full-Text
50635 46806 2014 5 PDF Available
Title
6H-Dibenzo[d,f-[1,3]diazepin-6-ylidene,5,7-dihydro-5,7-diphenylphosphanyl]: A new ligand for palladium-catalyzed Mizoroki–Heck coupling
Abstract

•A new diphosphine ligand DADPP, which is conveniently obtained.•DADPP has excellent properties in palladium catalyzed Heck coupling.•The highest TON of 96,000,000 was obtained with 4-bromobenzaldehyde as the substrate.•The yield of 95% was gained toward 4-nitrochlorobenzene with 0.05 mol.% [Pd(C3H5)Cl]2.

A novel and conveniently prepared diphosphine ligand 6H-Dibenzo[d,f-[1,3]diazepin-6-ylidene,5,7-dihydro-5,7-diphenylphosphanyl] (DADPP) combined with [Pd(C3H5)Cl]2 affords an efficient catalytic system for Mizoroki–Heck cross-coupling of aryl halides with alkenes. The system could give the yield of 95% for 4-chloronitrobenzene with 0.05 mol.% [Pd(C3H5)Cl]2. For the bromide-substituted substrates, the highest turnover number (TON) is up to 96,000,000.

Graphical abstractThe catalytic activity of [Pd(C3H5)Cl]2/DADPP in Mizoroki–Heck reaction of alkenes with various aryl halides is presented. The system could give the yield of 95% for 4-chloronitrobenzene with 0.05 mol.% [Pd(C3H5)Cl]2. For the bromide-substituted substrates, the highest turnover number (TON) is up to 96,000,000.Figure optionsDownload full-size imageDownload as PowerPoint slide

Keywords
Mizoroki–Heck coupling; Palladium; Phosphine; Aryl halide
First Page Preview
6H-Dibenzo[d,f-[1,3]diazepin-6-ylidene,5,7-dihydro-5,7-diphenylphosphanyl]: A new ligand for palladium-catalyzed Mizoroki–Heck coupling
Publisher
Database: Elsevier - ScienceDirect
Journal: Catalysis Communications - Volume 57, 5 December 2014, Pages 14–18
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis