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Evolving Oxeto-Indolinic Polycycles from Indoles by Means of a Visible-Light [2+2] Heterocycloaddition Dearomatization Process

preprint
submitted on 28.01.2020 and posted on 30.01.2020 by Javier Mateos, Alberto Vega-Peñaloza, Pietro Franceschi, Francesco Rigodanza, Philip Andreetta, Xavier Companyó, Giorgio Pelosi, Marcella Bonchio, Andrea Sartorel, Luca Dell'Amico
A large variety of highly functionalized N-containing polycycles (35 examples) are synthetized from simple indoles and aromatic ketones through a mild visible-light-driven [2+2]-heterocycloaddition process. Tetrahydrooxeto[2,3b]indole scaffolds, with up to three contiguous all-substituted stereo-centers are generated in high yield (up to >98%) and excellent site- regio- and diastereocontrol (>20:1). The use of visible light (405 or 465 nm) ensures enhanced performances by switching off undesired photodimerization reactions. Mechanistic investigations revealed that the operative reaction mechanism is dependent by the nature of the used ketone-substrate.

History

Email Address of Submitting Author

luca.dellamico@unipd.it

Institution

University of Padova

Country

Italy

ORCID For Submitting Author

0000-0003-0423-9628

Declaration of Conflict of Interest

The authors declare no conflict of interest

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