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Journal Articles European Journal of Organic Chemistry Year : 2023

Pd‐Catalyzed [3+2]‐Dehydrogenative Annulation Reactions

Yang Liu
  • Function : Author
Mikaël Le Roch
  • Function : Author
Alessia Mori
  • Function : Author
Alexandre Pradal
Giovanni Poli

Abstract

Abstract The significance of cross dehydrogenative couplings has increased considerably in recent years. This article revisits the [3+2] C−C/N−C, C−C/O−C and C−C/C−C annulation strategy, recently reported by our group, according to a Pd(II) catalyzed dehydrogenative variant. Our original report relied on Pd(0) catalysis, using α,β‐unsaturated‐γ‐oxy carbonyls as bis‐electrophiles and resonance‐stabilized acetamides or 3‐oxoglutarates as C/N and O/C or C/C bis‐nucleophiles, respectively. In this more modern and straightforward Pd(II)‐catalyzed dehydrogenative approach, β,γ‐unsaturated carbonyl derivatives replace α,β‐unsaturated‐γ‐oxy carbonyls as bis‐electrophiles. Our study includes experimental optimization and showcases the synthetic versatility in the formation of diverse heterocyclic structures, such as bicyclic lactams, furo‐cycloalkanones and bicycloalkane‐diones. Furthermore, a mechanism is proposed to elucidate the underlying processes involved in these reactions.
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Dates and versions

hal-04216991 , version 1 (27-09-2023)

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Yang Liu, Mikaël Le Roch, Alessia Mori, Alexandre Pradal, Giovanni Poli, et al.. Pd‐Catalyzed [3+2]‐Dehydrogenative Annulation Reactions. European Journal of Organic Chemistry, 2023, 26 (38), ⟨10.1002/ejoc.202300710⟩. ⟨hal-04216991⟩
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