1152887-64-3Relevant academic research and scientific papers
A palladium-catalyzed dehydrative: N -benzylation/C-H benzylation cascade of 2-morpholinoanilines on water
Hikawa, Hidemasa,Ichinose, Risa,Kikkawa, Shoko,Azumaya, Isao
, p. 1297 - 1305 (2018)
A strategy for the palladium-catalyzed dehydrative tandem benzylation of 2-morpholinoanilines with benzyl alcohols has been developed. This cascade reaction is 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 proceeds chemoselectively at the benzylic position of N-benzyl-2-morpholinoaniline to form a new C(sp3)-C (sp3) bond. KIE experiments show that C-H bond activation is involved in the rate-determining step (KIE = 2.7). A Hammett study of 2-morpholinoanilines gives a negative ρ value, suggesting that there is a build-up of positive charge in the transition state. A on water protocol, which affords 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.
Insertion of arynes into N-halo bonds: A direct approach to O -haloaminoarenes
Hendrick, Charles E.,McDonald, Stacey L.,Wang, Qiu
supporting information, p. 3444 - 3447 (2013/07/26)
A new approach to access o-haloaminoarenes has been achieved by insertion of arynes into a nitrogen-halide bond (N-X). This transition-metal-free transformation displays a broad substrate scope of arynes, good compatibility with functional groups, and high regioselectivity. Representative transformations of the o-haloaminoarenes are described to highlight their utility for rapid access to diversely functionalized aminoarene derivatives.
