Selective α-Methylation of Aryl Ketones Using Quaternary Ammonium Salts as Solid Methylating Agents | Zendy

Johanna Templ | Zendy; Michael Schnürch | Zendy

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Selective α-Methylation of Aryl Ketones Using Quaternary Ammonium Salts as Solid Methylating Agents

Author(s) -

Johanna Templ,

Michael Schnürch

Publication year - 2022

Publication title -

the 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) - chemistry , ammonium , anisole , aryl , solvent , iodide , methyl iodide , regioselectivity , methylation , organic chemistry , ammonium iodide , catalysis , alkyl , gene , biochemistry

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%.

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