Alcohol

Catalysis

Nucleophilic addition

Cascade reaction

Divergent synthesis

Stereochemistry

Physical chemistry

Polymer

Medicinal chemistry

Combinatorial chemistry

Organic chemistry

Amine gas treating

Nucleophile

Propargyl

Alkyne

Surface modification

Conjugated system

Oxindole

Chemistry

Propargyl alcohol

ACS Catalysis

[3,4]-Fused oxindoles are the core structures of the naturally occurring oxindole alkaloids, and the fused tricyclic structures have distinguished themselves with unique biological activities. Herein, we developed a synthetic strategy for divergent synthesis of diverse types of [3,4]-seven- or six-membered ring-fused 3-alkenyl-oxindoles incorporating benzazepine and significant building blocks from propargyl alcohols via the cascade nucleophilic substitution/site-selective hydride transfer/cyclization process unprecedentedly. In addition, a variety of nucleophiles, including H2O, were available for controllable construction of a wide range of conjugated alkenes, conjugated ketones, and allyl alcohols encompassing natural products and pharmaceutical motifs with the utilization of 4-amine substituted isatins and widespread terminal alkyne-derived propargyl alcohols. Furthermore, the synthetic utility of the methodology and mechanistic studies also were well presented.

Divergent Synthesis of [3,4]-Fused 3-Alkenyl-Oxindoles via Propargyl Alcohol-Triggered C(sp<sup>3</sup>)–H Functionalization

Divergent Synthesis of [3,4]-Fused 3-Alkenyl-Oxindoles via Propargyl Alcohol-Triggered C(sp3)–H Functionalization

Divergent Synthesis of [3,4]-Fused 3-Alkenyl-Oxindoles via Propargyl Alcohol-Triggered C(sp³)–H Functionalization