Cu-facilitated C-O bond formation using N-hydroxyphthalimide: efficient and selective functionalization of benzyl and allylic C-H bonds.
A highly efficient protocol for the benzyl or allylic C-H functionalization of simple hydrocarbons has been developed using stoichiometric amounts of N-hydroxyphthalimide and PhI(OAc)2 in the presence of CuCl catalyst. The reaction was revealed to proceed via a radical pathway, in which phthalimide N-oxyl (PINO) radical plays a dual role, serving as a catalytic hydrogen abstractor from hydrocarbons as well as a stoichiometric reagent to couple with the resultant alkyl radicals.
Lee
Ji Min
JM
Department of Chemistry and School of Molecular Science (BK21), Korea Advanced Institute of Science and Technology, Daejeon 305-701, Republic of Korea.
Park
Eun Ju
EJ
Cho
Seung Hwan
SH
Chang
Sukbok
S