We found a match
Your institution may have rights to this item. Sign in to continue.
- Title
Pd‐Catalyzed [3+2]‐Dehydrogenative Annulation Reactions.
- Authors
Liu, Yang; Roch, Mikaël Le; Mori, Alessia; Pradal, Alexandre; Poli, Giovanni; Oble, Julie
- 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.
- Subjects
ANNULATION; LACTAMS; CATALYSIS; PALLADIUM
- Publication
European Journal of Organic Chemistry, 2023, Vol 26, Issue 38, p1
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202300710