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Pd-Catalyzed Formal [2 + 2]-Retrocyclization of Cyclobutanols via 2-Fold Csp3-Csp3 Bond Cleavage
Sergio Parra-García1, Marina Ballester-Ibáñez1, José-Antonio García-López1
1Grupo de Química Organometálica, Departamento de Química Inorgánica, Facultad de Química, Universidad de Murcia, E-30100 Murcia, Spain.
Abstract:
In this work, we describe the unexpected 2-fold Csp3-Csp3 bond cleavage suffered by cyclobutanols in the presence of a catalytic amount of Pd(OAc)2 and promoted by the bulky biaryl JohnPhos ligand. Overall, the sequential cleavage of a strained and an unstrained Csp3-Csp3 bond leads to the formal [2 + 2]-retrocyclization products, namely, styrene and acetophenone derivatives. This procedure might enable the use of cyclobutanols as masked acetyl groups, resisting harsh conditions in organic synthesis.
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