Open AccessSelective α-Methylation of Aryl Ketones Using Quaternary Ammonium Salts as Solid Methylating Agents
Author(s) -
Johanna Templ,
Michael Schnürch
Publication year - 2022
Publication title -
journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.1c03158
Subject(s) - ammonium , anisole , aryl , chemistry , solvent , iodide , methylation , regioselectivity , methyl iodide , organic chemistry , ammonium iodide , catalysis , alkyl , biochemistry , gene
We describe the use of phenyl trimethylammonium iodide (PhMe 3 NI) as an alternative methylating agent for introducing a CH 3 group in α-position to a carbonyl group. Compared to conventional methylating agents, quaternary ammonium salts have the advantages of being nonvolatile, noncancerogenic, and easy-to-handle solids. This regioselective method is characterized by ease of operational setup, use of anisole as green solvent, and yields up to 85%.