Work

Brønstead Acid-Catalyzed Regiodivergent Hydroindolation of Indoles: Temperature-Controlled Markovnikov and Anti-Markovnikov Addition

Year: 2025

Type: article

Abstract: Brønsted acid-catalyzed, regiodivergent hydroindolation of indoles with terminal aryl alkynes was developed, affording bis(indolyl)alkanes in good to excellent yields. Systematic investigations revealed that temperature variation plays a key role in determining the regioselectivity of anti-Markovnikov and Markovnikov addition reactions. The reaction proceeds efficiently under transition metal-free conditions in an environmentally benign water/alcohol solvent system, using readily available and inexpensive p-toluenesulfonic acid (TsOH) as the catalyst. Control experiments and mechanistic studies support distinct reaction pathways for each regioisomer.

Source: International Journal of Molecular Sciences

DOI: 10.3390/ijms26188757

Authors: Asaithampi Ganesan, Yong-Uk Kwon

Institution: Ewha Womans University

Language: English

Topic: Synthesis of Indole Derivatives

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $3,499

Funders: National Research Foundation, Ewha Womans University, National Research Foundation of Korea, Ministry of Science and ICT, South Korea