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

Chemical Science
Javier MateosLuca Dell'Amico

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.

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Citations

Jul 13, 2021·European Journal of Organic Chemistry·Marina SicignanoJosé Alemán
Dec 29, 2020·The Journal of Organic Chemistry·Martins S OderindeJames Kempson
Nov 19, 2021·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Roberto TinelliLuca Capaldo

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Methods Mentioned

BETA
NMR
X-ray

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