One-Pot, Metal-Free Synthesis of Allyl Sulfones in Water.
J Org Chem
; 89(2): 835-843, 2024 Jan 19.
Article
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| MEDLINE
| ID: mdl-38194354
ABSTRACT
A one-pot dehydration cross-coupling reaction between allyl alcohols and sodium sulfinates that provides allyl sulfones in good to excellent yields is presented. Its broad substrate scope includes symmetrical and asymmetrical α,α-diaryl- and α-aryl-substituted allylic alcohols and aryl and alkyl sodium sulfinates. For asymmetrical allylic substrates, the E isomer predominates with examples of excellent stereoselectivity. Control experiments provide the basis for a proposed radical-mediated mechanism. The metal-free procedure applies cheap and commercially available tetrabutylammonium tribromide as the catalyst and H2O as the solvent. Notable features of this simple, efficient, weakly toxic, and environmentally benign strategy include mild and convenient operating conditions and readily accessible starting materials.
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Banco de datos:
MEDLINE
Idioma:
En
Revista:
J Org Chem
/
J. org. chem
/
Journal of organic chemistry
Año:
2024
Tipo del documento:
Article