期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 364, 期 17, 页码 2932-2938出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202200613
关键词
synthetic methods; sulfur; alkenes; alkynes; halogens
资金
- MICINN [PID2020-115789GB-C21]
- NextGenerationEU/PRTR [PDC2021-120825-C21]
- Junta de Castilla y Leon and FEDER [BU049P20]
- la Caixa Foundation [LCF/PR/PR18/51130007, CAIXA-UBU001]
- Junta de Castilla y Leon (Consejeria de Educacion)
- Fondo Social Europeo
A tandem 1,3-sulfur migration followed by iodocyclization reaction has been developed to synthesize indene-based beta-iodoalkenyl sulfides in the presence of NIS in HFIP. The choice of reaction media is crucial in promoting the reaction, and the proposed mechanism involving NIS activation by HFIP and favoring sulfur migration is supported by experimental evidence. Additionally, the suitability of the synthesized compounds as building blocks for subsequent C-C bond-forming reactions has been demonstrated.
A tandem 1,3-sulfur migration followed by iodocyclization reaction of propargylic sulfides in the presence of NIS in HFIP has been developed to synthesize indene-based beta-iodoalkenyl sulfides. The choice of the reaction media is crucial to promote the reaction. The proposed mechanism involving the initial NIS activation by HFIP and favoring the sulfur migration of the starting propargylic thioether via cationic intermediates is experimentally supported. In addition, the suitability of selected indene-based beta-iodoalkenyl sulfides as building blocks for subsequent C-C bond-forming reactions has been demonstrated.
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