Direct Synthesis of Benzo[<i>b</i>]fluorenyl Thiophosphates via Tandem Cyclization of Diynols with (RO)<sub>2</sub>P(O)SH
Sha Du, Shimin Jiang, Ruchun Yang, Fengyan Jin, Haiyang Huang, Wan‐Fa Tian, Zhao‐Zhao Zhou, Xian‐Rong Song, Qiang Xiao
Abstract
A general and metal-free protocol for the construction of benzo[ b ]fluorenyl thiophosphates was developed through the cascade cyclization of easily prepared diynols and (RO) 2 P(O)SH, with water as the only byproduct. The novel transformation involved the allenyl thiophosphate as the key intermediate, followed by Schmittel-type cyclization to achieve the desired products. Notably, (RO) 2 P(O)SH acted not only as a nucleophile but also as an acid-promoter to initiate the reaction.
Topics & Concepts
ChemistryThiophosphateTandemNucleophileStereochemistryCascade reactionCombinatorial chemistryMedicinal chemistryTransformation (genetics)Organic chemistryCatalysisGeneMaterials scienceComposite materialBiochemistrySulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsSynthesis of Indole Derivatives