1 research outputs found
Photoinduced Alkyl/Aryl Radical Cascade for the Synthesis of Quaternary CF<sub>3</sub>‑Containing Oxindoles and Indoline Alkaloids
Metal-
and additive-free, photoinduced decarboxylative
radical
alkylation–cyclization of CF3-acrylamides with
alkyl redox-active esters provided the corresponding quaternary CF3-oxindole derivatives in good yields. Notably, diaryliodonium
salts also efficiently participated in the arylation–cyclization
of CF3-acrylamides in environmentally benign H2O as a solvent. The present approach has been extended for the concise
synthesis of CF3-attached indoline alkaloid analogues,
i.e., CF3-(±)-desoxyeseroline, CF3-(±)-esermethole,
and CF3-(±) progesterone receptor antagonists. The
preliminary mechanistic studies revealed that the reaction is likely
to proceed through initial photoexcitation of redox-active ester/diaryliodonium
salts followed by the SET process with acrylamide