Work

Skeletal recasting of benzo[c][1,2]dithiol-3-ones for the construction of 3-hydroxybenzo[b]thiophenes

Year: 2025

Type: article

Abstract: An unprecedented carbene-induced skeletal recasting of benzo[c][1,2]dithiol-3-ones is demonstrated herein. This Pd-catalyzed molecular editing of benzo[c][1,2]dithiol-3-ones serves as a powerful platform for the streamline assembly of diverse 3-hydroxybenzo[b]thiophenes in decent yields under mild conditions by taking advantage of diazo compounds as the carbene precursors. The current skeletal recasting reaction is operationally simple (not sensitive to water and air), scalable, and well-suited for late-stage functionalization of complex diazo compounds derived from marketed drugs and natural products, in which valuable 3-hydroxybenzo[b]thiophenes could be achieved via formal [4 + 1] cyclization reaction. A novel palladium-catalyzed skeletal recasting reaction for the streamline assembly of 3-hydroxybenzo[b]thiophene is demonstrated herein, which represents the first example for carbene-induced skeletal editing of benzo[c][1,2]dithiol-3-ones by using diazo compounds as the carbene precursors.

Source: Green Synthesis and Catalysis

DOI: 10.1016/j.gresc.2025.08.001

Authors: Xuan Kong, Jing Zheng, Zhengheng Li, Yuan Yin, Yushang Qin, Yao Zhou

Institution: Hubei Normal University

Language: English

Topic: Cyclopropane Reaction Mechanisms

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

Funders: National Natural Science Foundation of China, Natural Science Foundation of Hubei Province, Science and Technology Department of Hubei Province

Awards: G2183401273, G2864590881, G6965736632