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Visible‐Light Photoredox Alkylation of Heteroaromatic Bases Using Ethyl Acetate as Alkylating Agent
Author(s) -
Győrfi Nándor,
Kotschy András,
Gyuris Márió
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202001113
Subject(s) - chemistry , hydrogen atom , photoredox catalysis , alkylation , visible spectrum , photochemistry , combinatorial chemistry , electron transfer , organic chemistry , catalysis , photocatalysis , alkyl , physics , optoelectronics
An efficient room‐temperature visible‐light photoredox α ‐acyloxyalkylation reaction of N ‐heteroarenes is reported, which relies on the use of ethyl acetate as a cheap and non‐conventional radical source. The direct C(sp 2 )‐C(sp 3 ) coupling was extended to a diverse set of mono‐, bi‐, and tricyclic of N ‐heteroaromatics, and the optimized photoredox protocol was successfully performed on a multigram scale. The scope of the alkylating agent was also explored and a plausible mechanism was proposed, involving photoinduced single‐electron transfer and hydrogen‐atom transfer processes.