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

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

Journal

Advanced Synthesis & Catalysis
ISSN: 1615-4169 , E-ISSN: 1615-4150

Output data

Year: 2023, Volume: 365, Number: 21, Pages: 3690-3703 Pages count : 14 DOI: 10.1002/adsc.202300833

Authors

Shirinian Valerii Z. ¹ , Balakhonov Roman ¹ , Mekeda Igor ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences 47, Leninsky prosp. 119991 Moscow Russian Federation

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.

Shirinian V.Z. , Balakhonov R. , Mekeda I.
DABCO‐Promoted Selective Photochemical C−N Coupling: Access to Unsymmetrical Azahelicenes
Advanced Synthesis & Catalysis. 2023. V.365. N21. P.3690-3703. DOI: 10.1002/adsc.202300833 WOS Scopus OpenAlex

Web of science:	WOS:001072898500001
Scopus:	2-s2.0-85172678112
OpenAlex:	W4386759780

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OpenAlex	12
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