The development of highly selective methods for the synthesis of 1,3-dienes is a challenge to synthetic chemistry. The development of novel methods to overcome these challenges are highly desirable due to their ubiquitous nature. Herein, is reported a highly selective approach for the synthesis of 1,3-dienes using the ruthenium hydride catalyzed silylvinylation of silicon-tethered homopropargyl alcohols using ethylene gas. This method allows for the silylvinylation of terminal alkynes using ethylene at 80 psi and affords solely the Z-isomer. This method is applicable to substrates with aryl and alkyl substitution at the propargyl and homopropargyl positions and has been utilized in the synthesis of 5- and 6-membered oxasilacycles. Additionally, the scope and mechanism of this silylvinylation reaction will be presented.

Ruthenium hydride catalyzed silylvinylation of terminal alkynes under high pressure ethylene atmosphere

252nd National Meeting (2016)

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