Hikawa, Hidemasa published the artcileA palladium-catalyzed dehydrative N-benzylation/C-H benzylation cascade of 2-morpholinoanilines on water, SDS of cas: 6214-45-5, the main research area is morpholinoaniline benzyl alc palladium catalyst tandem chemoselective dehydrative benzylation; diphenylethyl morpholinoaniline preparation green chem.
A strategy for the palladium-catalyzed dehydrative tandem benzylation of 2-morpholinoanilines with benzyl alcs. was developed. This cascade reaction was devised as a straightforward and efficient synthetic route for N-(1,2-diphenylethyl)-2-morpholinoanilines in moderate to good yields (50-81%). The dehydrative sp3 C-H bond benzylation proceeded chemoselectively at the benzylic position of N-benzyl-2-morpholinoaniline to form a new C(sp3)-C (sp3) bond. KIE experiments showed that C-H bond activation was involved in the rate-determining step (KIE = 2.7). A Hammett study of 2-morpholinoanilines gave a neg. ρ value, suggested that there was a build-up of pos. charge in the transition state. A “”on water”” protocol, which afforded the corresponding desired products with water as the sole co-product, can be achieved under mild reaction conditions without the need for bases or other additives in an atom-economical process.
Green Chemistry published new progress about Benzylation (chemoselective, dehydrative). 6214-45-5 belongs to class alcohols-buliding-blocks, name is (4-Butoxyphenyl)methanol, and the molecular formula is C11H16O2, SDS of cas: 6214-45-5.
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts