DABCO‐Promoted Selective Photochemical C−N Coupling: Access to Unsymmetrical Azahelicenes.

Autor:	Balakhonov, R. Yu., Mekeda, I. S., Shirinian, V. Z.
Předmět:	CHARGE exchange SCISSION (Chemistry) CHEMOSELECTIVITY RING formation (Chemistry) RADICALS (Chemistry) ELECTROPHILES IRRADIATION PHOTOCYCLIZATION ELECTRON donors
Zdroj:	Advanced Synthesis & Catalysis; 11/7/2023, Vol. 365 Issue 21, p3690-3703, 14p
Abstrakt:	A multifaceted study on the effect of various factors on the efficiency of photocyclization of naphthofuran O‐acyl oximes was performed. It showed that without any additives or in the presence of electron acceptors, the reaction occurs by a radical pathway and with low chemoselectivity, while DABCO promotes intramolecular cyclization to give naphthofuroquinolines (NFQs) in 34–87% yields. The iminyl radical formed under UV irradiation in the presence of DABCO due to single electron transfer (SET) and N−O bond cleavage undergoes selective intramolecular homolytic aromatic substitution (HAS) with formation of a new C−N bond. This route to quinoline‐annulated scaffolds is based on the use of DABCO both as an electron transfer agent and a proton acceptor. [ABSTRACT FROM AUTHOR]
Databáze:	Complementary Index
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