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The Chemoselective, Enantiospecific Cross-Coupling of Secondary Boronic Esters and the Stability of Mesoporous Silica Supports for Pd Catalysis

GLASSPOOLE, BEN WILLIAM
Fonte: Quens University Publicador: Quens University
Tipo: Tese de Doutorado
EN; EN
Relevância na Pesquisa
36.712786%
The Suzuki-Miyaura Cross-Coupling of aryl halides and aryl boronic esters has become one of the most important and oft used C-C bond forming reactions in industry and academia alike. Recently, substantial effort has been invested in expanding this reaction to include alkyl boronic esters as coupling partners, though until recently, success has been limited to primary alkyl boronic esters. Secondary alkyl boronic esters, with the inherent possibility of being chiral, have proven to be more difficult to couple. As a means of expanding our program on the enantio- and regioselective hydroboration of styrene derivatives, we sought to develop conditions that could couple benzylic (secondary) boronic esters. Not only was the coupling to aryl iodides achieved in moderate to good yield with a commercially available (and relatively cheap) catalyst system and phosphine, but the coupling reaction proceeds with almost complete retention of the stereochemistry installed during the hydroboration reaction. Interestingly, these conditions leave primary (linear) alkyl boronic esters completely untouched. Further examination of the chemoselectivity of the reaction revealed that, despite being unable to cross-couple strictly aliphatic secondary boronic esters...