Solvent-controlled nucleophilic trifluoromethylthiolation of Morita–Baylis–Hillman carbonates: dual roles of DABCO in activating the Zard's trifluoromethylthiolation reagent and the MBH carbonates

Autor:	Yin Wei, Xing Fan, Min Shi, Hai-Bin Yang
Rok vydání:	2015
Předmět:	Solvent Allylic rearrangement chemistry.chemical_compound Dual role Nucleophile Chemistry Reagent Organic Chemistry Regioselectivity Organic chemistry DABCO
Zdroj:	Organic Chemistry Frontiers. 2:1088-1093
ISSN:	2052-4129
DOI:	10.1039/c5qo00198f
Popis:	A novel amine-catalyzed nucleophilic trifluoromethylthiolation between Morita–Baylis–Hillman carbonates and O-octadecyl-S-trifluorothiolcarbonate has been developed. The regioselectivity of this reaction can be controlled by choosing different solvents, affording primary allylic SCF3 products in THF and secondary allylic SCF3 products in CHCl3 as major products. The mechanistic investigation indicated that DABCO plays a dual role in activating the Zard's trifluoromethylthiolation reagent and the MBH carbonates.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::bdae2b1273eac37fe08b57e908097152 https://doi.org/10.1039/c5qo00198f Zobrazit plný text záznamu