Visible-Light-Driven Synthesis of Alkenyl Thiocyanates: Novel Building Blocks for Diverse Sulfur-Containing Molecular Assembly

04 July 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

The first visible-light-induced protocol for the general preparation of alkenyl thiocyanates from alkenyl bromides is presented. The reaction is simple, proceeds under very mild conditions and demonstrates broad functional group tolerance. Additionally, a flow protocol was developed to enable efficient scale-up of alkenyl thiocyanate synthesis, further enhancing the practicality and value of the method. Importantly, these alkenyl thiocyanates serve as valuable building blocks for the construction of diverse families of sulfur-containing molecules through trifluoromethylation, cycloaddition, oxidations, and C–S or C–P bond forming reactions.

Keywords

Photochemistry
Flow chemistry
Building block
C–S bond formation

Supplementary materials

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CONTENTS 1. General considerations 2. Continuous flow protocol 3. General procedure for the synthesis and characterization data for the compounds 3 4. UV-Vis spectra 5. Computational studies 6. NMR titration experiments 7. Binding constant calculation 8. Quantum yield measurement 9. Light on/off studies 10. General procedure for the preparation of compounds 7, 8, 9, 10, 11 and 12 11. Copies of the NMR spectra
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