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User‐Friendly Methylation of Aryl and Vinyl Halides and Pseudohalides with DABAL‐Me 3
Author(s) -
Cooper Thea,
Novak Andrew,
Humphreys Luke D.,
Walker Matthew D.,
Woodward Simon
Publication year - 2006
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200505405
Subject(s) - chemistry , halide , catalysis , aryl , adduct , methylation , organic chemistry , oxygen , polymer chemistry , biochemistry , alkyl , gene
An extremely technically simple cross‐methylation of aryl and vinyl halides and pseudohalides using an air‐stable adduct of trimethylaluminium with a Pd(0) catalyst supported by commercially available biarylphosphines gives excellent yields of methylated products (mainly >95%). Reactions can be run with either 0.5 mol % catalyst or without requiring the exclusion of atmospheric oxygen or the drying of solvents in some cases. A wide variety of functional groups is tolerated including CN, OH, CO 2 R, CHO and NO 2 .