Selenium Transfer from Secondary Phosphine Selenides to Aminoacetylenic Ketones: Access to 1,2-Dihydro-3H-pyrrole-3-selones with a Stable C═Se Bond

Abstract

Secondary phosphine selenides were found to react with γ-aminoacetylenic ketones (80−85 °C, MeCN, 17−40 h) to afford 1,2-dihydro-3H-pyrrole-3-selones in 48−80% yields, products of unprecedented selenium transfer from the P�Se bond to replace the carbonyl oxygen and to form dihydro-3H-pyrrole-3selones having a C�Se bond stable under ambient conditions.