Science of Synthesis

Molander, G. A.; Ryu, D., Science of Synthesis: C-1 Building Blocks in Organic Synthesis, (2014) 2, 61.

Trimethylaluminum is extremely flammable, but a user-friendly, air-stable surrogate has been employed to methylate a variety of aryl and alkenyl electrophiles. Thus, the trimethylaluminum adduct of 1,4-diazobicyclo[2.2.2]octane (DABAL-Me3, ‌30‌) is highly effective for the methylation of substrates containing nitrile, ester, alcohol, nitro, phenol, and aldehyde functional groups (‌Scheme 35‌). Chloride, bromide, and trifluoromethanesulfonate leaving groups are all tolerated, and thus the method appears highly competitive with that of many of the methylboron reagents described above.[‌39‌]

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Me	Me	>88	[‌88‌]
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8-Mee	Me	>88	[‌88‌]
8-Mee	Me	>88	[‌88‌]
8-MM8M8	Me	>88	[‌88‌]
8-M8MM8M8	Me	>88	[‌88‌]
8-MeM8M8	Me	88	[‌88‌]
8-MMM8M8	Me	88	[‌88‌]
8-MMM8M8	Me	88	[‌88‌]
8-MMM8M8	Me	88	[‌88‌]
8-MMM8M8	Me	88	[‌88‌]
8-(M8M=MM)M8M8	Me	>88	[‌88‌]
8-(M8M=MM)M8M8	Me	88	[‌88‌]
8-MeMM8M8	Me	>88	[‌88‌]
8-MeMM8M8	Me	>88	[‌88‌]
8-MeMM8M8	MMe	>88	[‌88‌]
8-MeMM8M8	Me	>88	[‌88‌]
8-MeM8MM8M8	Me	88	[‌88‌]
8-MeM8MM8M8	Me	88	[‌88‌]
8-MMM8M8	Me	88	[‌88‌]
8-M8MM8M8	Me	88	[‌88‌]
8-M8MM8M8	Me	88	[‌88‌]
8-M8MM8M8	MMe	88	[‌88‌]
8-(MMMM8)M8M8	Me	88	[‌88‌]
8-MMMM8M8	Me	88	[‌88‌]
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References