Unified metal-free intermolecular Heck-type sulfonylation, cyanation, amination, amidation of alkenes by thianthrenation

Ming-Shang Liu, Hai-Wu Du, Huan Meng, Ying Xie and Wei Shu ()
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Ming-Shang Liu: Southern University of Science and Technology
Hai-Wu Du: Southern University of Science and Technology
Huan Meng: Southern University of Science and Technology
Ying Xie: Sichuan University of Science and Engineering
Wei Shu: Southern University of Science and Technology

Nature Communications, 2024, vol. 15, issue 1, 1-8

Abstract: Abstract Direct and site-selective C-H functionalization of alkenes under environmentally benign conditions represents a useful and attractive yet challenging transformation to access value-added molecules. Herein, a unified protocol for a variety of intermolecular Heck-type functionalizations of Csp2-H bond of alkenes has been developed by thianthrenation. The reaction features metal-free and operationally simple conditions for exclusive cine-selective C-H functionalization of aliphatic and aryl alkenes to forge C-C, C-N, C-P, and C-S bonds at room temperature, providing a general protocol for intermolecular Heck-type reaction of alkenes with nucleophiles (Nu = sulfinates, cyanides, amines, amides). Alkenes undergo cine-sulfonylation, cyanation, amination to afford alkenyl sulfones, alkenyl nitriles and enamines.

Date: 2024
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DOI: 10.1038/s41467-024-44746-w

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