Convergent Synthesis of Azabicycloalkenones Using Squaric Acid as Platform.

Abstract

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Catalytic C–C Bond Activations via Oxidative Addition to Transition Metals

“…The first catalytic example, a ruthenium-catalyzed C–C bond activation of cyclobutenediones to access cyclopentanones via a decarbonylative alkene insertion was reported by Mitsudo in 2000 . Yamamoto reported in 2006 a rhodium­(I)-catalyzed decarbonylative alkene insertion into cyclobutenediones 383 leading to azabicycloalkenones 389 (Scheme ) . This transformation is initiated by oxidative addition of cyclobutenedione 383 to rhodium­(I), resulting in the formation of rhoda­(III)­cyclopentenedione 385 .…”

“…181 Yamamoto reported in 2006 a rhodium(I)-catalyzed decarbonylative alkene insertion into cyclobutenediones 383 leading to azabicycloalkenones 389 (Scheme 73). 182 This transformation is initiated by oxidative addition of cyclobutenedione 383 to rhodium(I), resulting in the formation of rhoda(III)cyclopentenedione 385. Subsequent decarbonylation gave rhoda(III)cyclobutenone 386.…”

Capturing the Organic Species Derived from the C–C Cleavage and in Situ Oxidation of 1,2,3,4-Tetra(pyridin-4-yl)cyclobutane by [CuCN]n-Based MOFs

“…2 Cyclobutanes are essential structural motifs for numerous unique organic transformations. 6−8 The catalytic C−C bond activation of the functionalized cyclobutane derivatives including cyclobutanols, 9,10 cyclobutanones, 11,12 cyclobutendiones, 13,14 benzocyclobutanes, 15,16 and benzocyclobutenols 17,18 can offer unique routes to the construction of new organic molecules. To date, the cycloreversion of tetraarylcyclobutanes has rarely been documented.…”