PART 1: SYNTHESIS AND APPLICATION OF RECYCLABLE REAGENT AND CATALYST PART 2: SYNTHESIS OF A TRISACCHARIDE UNIT FROM K. PNEUMONIAE K-2044

Ph.DDOCTOR OF PHILOSOPH

Green Chemistry COMMUNICATION Development of a fluorous, oxime-based palladacycle for microwave-promoted carbon-carbon coupling reactions in aqueous media †

A thermally stable, fluorous oxime-based palladacycle has been developed and was shown to efficiently promote various carbon-carbon bond formation reactions (SuzukiMiyaura, Sonogashira and Stille) in aqueous media under microwave irradiation. The palladacycle gave extremely low levels of Pd leaching and could be reused five times with no significant loss of activity. The palladium-catalyzed carbon-carbon coupling reaction is an important tool for the synthesis of symmetric and nonsymmetric biaryls and over the decades, a wide variety of homogeneous catalytic systems have been developed for this transformation

Fluorous Oxime Palladacycle: A Precatalyst for Carbon–Carbon Coupling Reactions in Aqueous and Organic Medium

To facilitate precatalyst recovery and reuse, we have developed a fluorous, oxime-based palladacycle <b>1</b> and demonstrated that it is a very efficient and versatile precatalyst for a wide range of carbon–carbon bond formation reactions (Suzuki–Miyaura, Sonogashira, Stille, Heck, Glaser-type, and Kumada) in either aqueous or organic medium under microwave irradiation. Palladacycle <b>1</b> could be recovered through F-SPE in various coupling reactions with recovery ranging from 84 to 95% for the first cycle. Inductively coupled plasma optical emission spectrometry (ICP-OES) analyses of the Pd content in the crude product from each class of transformation indicated extremely low levels of leaching and the palladacycle could be reused four to five times without significant loss of activity

Fluorous oxime palladacycle: A precatalyst for carbon-carbon coupling reactions in aqueous and organic medium

10.1021/jo202482hJournal of Organic Chemistry7762729-2742JOCE