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Issue 25, 2020
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A visible-light Paternò–Büchi dearomatisation process towards the construction of oxeto-indolinic polycycles

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Abstract

A variety of highly functionalised N-containing polycycles (35 examples) are synthesised from simple indoles and aromatic ketones through a mild visible-light Paternò–Büchi process. Tetrahydrooxeto[2,3-b]indole scaffolds, with up to three contiguous all-substituted stereocenters, 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 photodimerisation side reactions. The reaction can be easily implemented using a microfluidic photoreactor with improved productivity (up to 0.176 mmol h−1) and generality. Mechanistic investigations revealed that two alternative reaction mechanisms can account for the excellent regio- and diastereocontrol observed.

Graphical abstract: A visible-light Paternò–Büchi dearomatisation process towards the construction of oxeto-indolinic polycycles

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Supplementary files

Article information


Submitted
16 Mar 2020
Accepted
15 Apr 2020
First published
16 Apr 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020,11, 6532-6538
Article type
Edge Article

A visible-light Paternò–Büchi dearomatisation process towards the construction of oxeto-indolinic polycycles

J. Mateos, A. Vega-Peñaloza, P. Franceschi, F. Rigodanza, P. Andreetta, X. Companyó, G. Pelosi, M. Bonchio and L. Dell’Amico, Chem. Sci., 2020, 11, 6532
DOI: 10.1039/D0SC01569E

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