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![Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F51444.jpg&w=3840&q=50)
Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
Published on: March 20, 2014
Light, medium, and heavy fluorous triarylphosphines exhibit comparable reactivities to triphenylphosphine in typical
Dennis P Curran1, Xiao Wang, Qisheng Zhang
1Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA. curran@pitt.edu
Abstract:
[reaction: see text] The relative reactivities of triphenylphosphine (PPh(3)) and three fluorous triarylphosphines [(p-R(F)(CH(2))(2)C(6)H(4))(n)PPh(3)(-)(n), where n = 1-3] have been compared in internal competition experiments. Product ratios were determined by (31)P NMR spectroscopy. The four phosphines have about the same reactivities in oxidation, alkylation, and Staudinger reactions and give comparable yields in a preparative Mitsunobu reaction. Previously observed rate and yield differences in Staudinger reactions of the fluorous phosphines are attributed to solubility effects, not reactivity differences. A light fluorous phosphine [(p-C(8)F(17)(CH(2))(2)C(6)H(4))PPh(2)] outperforms a commercially available resin-bound phosphine in a competitive benzylation experiment by a factor of about 4.
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