Copper-Catalyzed Syntheses of 3‑Allyl-3-arylthioindolin-2-imines and 3‑Allenyl-3-arylthioindolin-2-imines from 3‑Diazoindolin-2-imines

3-Allyl-3-arylthioindolin-2-imines
and 3-allenyl-3-arylthioindolin-
2-imines were synthesized via the copper-catalyzed reaction of 3-diazoindolin-2-imines
with allyl and propargyl aryl sulfides, respectively. The formation
of a sulfonium ylide through the reaction of allyl or propargyl aryl
sulfides with copper carbene species generated from 3-diazoindolin-2-imines
and subsequent [2,3]-sigmatropic rearrangement should be involved
in the cascade process. The procedure is general and highly efficient
for the construction of these 3,3-disubstituted indoline derivatives.