Abstract
A CH silylation of pyridines that seemingly proceeds through electrophilic aromatic substitution (SE Ar) is reported. Reactions of 2- and 3-substituted pyridines with hydrosilanes in the presence of a catalyst that splits the SiH bond into a hydride and a silicon electrophile yield the corresponding 5-silylated pyridines. This formal silylation of an aromatic CH bond is the result of a three-step sequence, consisting of a pyridine hydrosilylation, a dehydrogenative CH silylation of the intermediate enamine, and a 1,4-dihydropyridine retro-hydrosilylation. The key intermediates were detected by (1) H NMR spectroscopy and prepared through the individual steps. This complex interplay of electrophilic silylation, hydride transfer, and proton abstraction is promoted by a single catalyst.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
