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. © 2020 The Royal Society of Chemistry.
A visible-light Paternò-Büchi dearomatisation process towards the construction of oxeto-indolinic polycycles / Mateos, J.; Vega-Peñaloza, A.; Franceschi, P.; Rigodanza, F.; Andreetta, P.; Companyó, X; Pelosi, G.; Bonchio, M.; Dell'Amico, L.. - In: CHEMICAL SCIENCE. - ISSN 2041-6539. - 11:25(2020), pp. 6532-6538. [10.1039/d0sc01569e]
A visible-light Paternò-Büchi dearomatisation process towards the construction of oxeto-indolinic polycycles
Pelosi G.;
2020-01-01
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. © 2020 The Royal Society of Chemistry.| File | Dimensione | Formato | |
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