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Pd-PEPPSI-IPent-SiO2 : A Supported Catalyst for Challenging Negishi Coupling Reactions in Flow
Gregory A Price1, Abbas Hassan1,2, Nalin Chandrasoma1
1Department of Chemistry, York University, 4700 Keele Street, Toronto, Ontario, M3J1P3, Canada.
Abstract:
A silica-supported precatalyst, Pd-PEPPSI-IPent-SiO2 , has been prepared and evaluated for its proficiency in the Negishi cross-coupling of hindered and electronically deactivated coupling partners. The precatalyst Pd-PEPPSI-IPent loaded onto packed bed columns shows high catalytic activity for the room-temperature coupling of deactivated/hindered biaryl partners. Also for the first time, the flowed Csp3 -Csp2 coupling of secondary alkylzinc reagents to (hetero)aromatics has been achieved with high selectivity with Pd-PEPPSI-IPent-SiO2 . These couplings required residence times as short as 3 minutes to effect completion of these challenging transformations with excellent selectivity for the nonrearranged product.
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