Silicon-Mediated Synthesis of Selenoaldehydes and Selenoacylsilanes and Their Hetero Diels–Alder Reactions

Abstract

Bis(trimethylsilyl)selenide (HMDSS) reacts efficiently with aldehydes in the presence of CoCl ₂ ^.6H ₂ O to afford selenoaldehydes, which are trapped as Diels–Alder adducts by different dienes. The reaction can be applied to acylsilanes, to afford selenoacylsilanes, isolated as their cycloadducts.

Keywords:

• Diels–Alder cycloadditions
• selenoacylsilanes
• selenoaldehydes
• selenoheterocycles
• silyl-selenide

Acknowledgments

Dedicated to Professor Marian Mikołajczyk, CBMiM PAN in Łódź, Poland, on the occasion of his 70th birthday.

Financial support by the National Project “Stereoselezione in Sintesi Organica. Metodologie ed Applicazioni” (MIUR, Roma) is gratefully acknowledged. Mrs. B. Innocenti is acknowledged for technical support.