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Metal‐Free Direct C–H β‐Carbonyl Alkylation of Heteroarenes with Cyclopropanols Mediated by K 2 S 2 O 8
Author(s) -
Liu Qiang,
Wang Qiang,
Xie Guanqun,
Fang Zeyang,
Ding Shujiang,
Wang Xiaoxia
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.202000289
Subject(s) - chemistry , alkylation , reagent , thiazole , metal carbonyl , pyridazine , combinatorial chemistry , catalysis , phenanthroline , ring (chemistry) , metal , medicinal chemistry , organic chemistry
Direct C–H β‐carbonyl alkylation of heteroarenes under metal‐, acid‐ and photo‐catalyst free conditions has been achieved. A wide scope of substrates, such as various substituted quinolines and isoquinolines, pyridines, pyridazine, benzo[d]thiazole and phenanthroline, underwent the β‐carbonyl alkylation efficiently via K 2 S 2 O 8 ‐mediated ring‐opening of cyclopropanols. The corresponding β‐heteroarylated ketones were obtained in moderate to excellent yields and gram‐scale experiments further demonstrated the practicality of this synthetic protocol. The readily available reagents, mild and environmentally benign conditions make the method extremely attractive. The reaction mechanism is also proposed.