Work

General Light-Induced Pd-Catalyzed Allylic C–H Alkylation of Internal Alkenes: Direct Access to Tertiary and Quaternary Carbon Centers

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide Tertiary and quaternary carbon centers containing allylic systems are prevalent in natural products and drugs. Among existing approaches toward these valuable motifs, a direct allylic C–H alkylation is the most straightforward approach, which bypasses the requirement for prefunctionalization of allylic substrates. However, existing methods suffer from limited scope both in terms of alkenes and carbon nucleophiles. Herein, we report a light-induced Pd catalyzed method that overcomes these challenges, enabling the coupling of diverse internal alkenes with a range of carbon pronucleophiles including those with p K a > 20. In addition, this method provides direct access to the construction of tertiary and quaternary carbon centers in enantioselective fashion.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.5c15245

Authors: Subham Pradhan, Gaurav Prakash, Vladimir Gevorgyan

Institution: The University of Texas at Dallas

Language: English

Topic: Catalytic C–H Functionalization Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Welch Foundation, University of Texas at San Antonio, National Institutes of Health, National Institute of General Medical Sciences