Iodomethane

Selective Methylation of Amides, N-Heterocycles, Thiols, and Alcohols with Tetramethylammonium Fluoride

“…As such, substantial efforts have been devoted to this field (see Figure ). The methylation of amides is traditionally done with frequently unstable, volatile, or toxic methylating agents such as iodomethane, dimethyl sulfate, or chloromethyldimethylsilyl chloride and frequently requires an excess of a strong base. Alternative strategies include the reductive methylation with formaldehyde as a methylcarbon source or the transition-metal-catalyzed methylation of amides with methanol .…”

Frontispiece: The Deuterated “Magic Methyl” Group: A Guide to Site‐Selective Trideuteromethyl Incorporation and Labeling by Using CD3 Reagents

“…Analogous to methyl iodide, CD 3 I is one of the main trideuteromethylation reagents. [42] Because iodide is a good leaving group, it is especially suitable for nucleophilic substitution reactions, and the weak CÀ I bond makes it very prone to oxidative insertion of a transition-metal catalyst. Reported in 1969, trideuteromethylation of aryl bromides with CD 3 I was achieved via the Wurtz-Fittig reaction, which relies on the use of very reactive sodium (Scheme 8a).…”

Abiotic Methylation of Tetrabromobisphenol A (TBBPA) with the Occurrence of Methyl Iodide in Aqueous Environments

“…CH 3 I is a good methyl group donor. It is able to methylate many metals, metalloids in the environment, and organic compounds in chemical synthesis through abiotic pathways. − CH 3 I can be naturally formed by algae, fungi, and higher plants (paddy rice, wheat, and daikon radish) and exists in the air, oceans, freshwater, and terrestrial ecosystems. − In addition, CH 3 I is widely used as an agricultural soil fumigant and released to freshwater through runoff, causing high concentrations in aqueous environments. After CH 3 I is applied to a soil column in laboratory-simulated experiment, the early leaching concentrations of CH 3 I can exceed 10 μg L –1 .…”