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Photoredox‐Catalysed Decarboxylative Alkylation of N‐Heteroarenes with N ‐(Acyloxy)phthalimides
Author(s) -
Cheng WanMin,
Shang Rui,
Fu MingChen,
Fu Yao
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201605640
Subject(s) - phthalimides , alkylation , chemistry , catalysis , regioselectivity , reactivity (psychology) , iridium , medicinal chemistry , photocatalysis , organic chemistry , phthalimide , medicine , alternative medicine , pathology
An iridium photoredox catalyst in combination with either a stoichiometric amount of Brønsted acid or a catalytic amount of Lewis acid is capable of catalyzing regioselective alkylation of N‐heteroarenes with N ‐(acyloxy)phthalimides at room temperature under irradiation. A broad range of N‐heteroarenes can be alkylated using a variety of secondary, tertiary, and quaternary carboxylates. Mechanistic studies suggest that an Ir II /Ir III redox catalytic cycle is responsible for the observed reactivity.