%0 Journal Article
%A Zhao, Ren
%A Lu, Wenjun
%D 2017
%T Palladium-Catalyzed β‑Mesylation of Simple
Amide via Primary sp3 C–H Activation
%U https://acs.figshare.com/articles/journal_contribution/Palladium-Catalyzed_Mesylation_of_Simple_Amide_via_Primary_sp_sup_3_sup_C_H_Activation/4776553
%R 10.1021/acs.orglett.7b00536.s001
%2 https://ndownloader.figshare.com/files/7842535
%K intramolecular S N 2 processes
%K β- fluoroamides
%K methanesulfonic anhydride
%K CH
%K β- lactams
%K OH
%K cyclic alkanes
%K electron-deficient benzyl compounds
%K Simple Amide
%K sp
%K amide substrates
%K β- mesylation
%K Ms 2 O
%K β- mesylated amide products
%X A β-mesylation of primary sp3 C–H bonds
from simple amides with methanesulfonic anhydride (Ms2O)
has been established successfully at 80 °C in a Pd(OAc)2 (catalyst)/K2S2O8 (oxidant)/CF3CH2OH (solvent) system. These amide substrates
involve N-monosubstituted linear, branch, or cyclic
alkanes, and electron-deficient benzyl compounds. The β-mesylated
amide products can be converted easily to β-fluoroamides or
β-lactams through inter- or intramolecular SN2 processes.
%I ACS Publications