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Updated: Oct 25, 2026
![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
Crossing the Reactivity Threshold: Phosphonate-Directed, Gold-Catalyzed Oxygen Transfer to Alkynyl Phosphonates
Polina F Kotikova1, Karina O Mahmedova1, Vadim Yu Kukushkin1,2
1Saint Petersburg State University, Universitetskaya Nab. 7/9, 199034Saint Petersburg, Russian Federation.
Abstract:
The first gold-catalyzed oxygen-transfer reaction of alkynyl phosphonates is reported, providing regioselective access to oxazol-4-yl phosphonates through a formal (2+2+1) assembly. The low intrinsic reactivity of alkynyl phosphonates was overcome by pairing the weakly activating phosphonate group with a strongly π-acidic phosphite-gold(I) catalyst and an electronically attenuated O-transfer reagent. The synthetic value is underscored by a gram-scale synthesis, downstream elaborations to the phosphonic acids, and access to phosphonate analogues of bioactive oxazoles.
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