Publication: Pd-catalyzed formal [2+2]-retrocyclization of cyclobutanols via two-fold Csp3–Csp3 bond cleavage
Authors
Parra-García, Sergio ; Ballester-Ibáñez, Marina ; García-López, José-Antonio
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Publisher
ACS
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DOI
https://doi.org/10.1021/acs.joc.3c01750
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info:eu-repo/semantics/article
Description
© 2024 The Authors
This document is the accepted version of a published work that appeared in final form in The Journal of Organic Chemistry
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To access the final edited and published work see: https://doi.org/10.1021/acs.joc.3c01750
Abstract
In this work we describe the unexpected two-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 ace- tophenone derivatives. This procedure might enable the use of cyclobutanols as masked acetyl groups resisting harsh condi- tions in organic synthesis.
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Citation
The Journal of Organic Chemistry, 2024, 89, 2, 882-886
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