In-situ Kinetic Studies of Rh(II)-Catalyzed C-H Functionalization to Achieve High Catalyst Turnover Numbers.

ABSTRACT: Detailed kinetic studies on the functionalization of unactivated hydrocarbon sp³ C-H bonds by dirhodium-catalyzed reaction of aryldiazoacetates revealed that the C-H functionalization step is rate-determining. The efficiency of this step was increased by using the hydrocarbon as solvent and using donor/acceptor carbenes with an electron-withdrawing substituent on the aryl donor group. The optimum catalyst for these reactions is the tetraphenylphthalimido derivative Rh2(R-TPPTTL)₄ and a further beneficial refinement was obtained by using N,N'-dicyclohexylcarbodiimide as an additive. Under the optimum conditions with a catalyst loading of 0.001 mol %, effective enantioselective C-H functionalization (66-97% yield, 83-97% ee) was achieved of cycloalkanes wi

SUBMITTER: Wei B 

PROVIDER: S-EPMC10237631 | biostudies-literature | 2022 Nov

REPOSITORIES: biostudies-literature