C2-Selective silylation of pyridines by a rhodium–aluminum complex
Naofumi Hara, Nao Uemura, Yoshiaki Nakao
Abstract
We have developed a C2-selective mono-silylation of a variety of pyridines using a Rh-Al complex. Both the site- and mono-selectivity are controlled via the pyridine coordination to the Lewis-acidic Al center prior to the activation of the pyridine C(2)-H bond at the proximal Rh center. A reaction mechanism is proposed based on several mechanistic studies, including the isolation of a (2-pyridyl)silylrhodium intermediate.
Topics & Concepts
SilylationRhodiumChemistryAluminiumCombinatorial chemistryOrganic chemistryCatalysisCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsCoordination Chemistry and Organometallics