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Pd‐PEPPSI‐IPent‐SiO2, a Supported Catalyst for Challenging Negishi Coupling Reactions in Flow

A silica‐supported precatalyst, Pd‐PEPPSI‐IPent‐SiO2 (7), has been prepared and evaluated for its proficiency in the Negishi cross‐coupling of hindered and electronically deactivated coupling partners. Precatalyst 7 loaded into packed bed columns has shown very high catalytic activity for the room temperature coupling of deactivated/hindered biaryl partners. Also for the first time, the flowed sp3‐sp2 coupling of secondary alkylzinc reagents to (hetero)aromatics has been achieved with high selectivity using 7. These couplings required residence times as short as 3 minutes to affect complete conversion of these challenging transformations with excellent selectivity for the non‐rearranged product.

Authors:   Michael G Organ, Gregory A Price, Abbas Hassan, Andrew R Bogdan, Stevan W Djuric
Journal:   Angewandte Chemie International Edition
Year:   2017
Pages:   n/a
DOI:   10.1002/anie.201708598
Publication date:   08-Sep-2017
Facts, background information, dossiers
  • selectivity
  • temperature
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