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Pd-Catalyzed Diastereoselective Trifluoromethylthiolation of Functionalized Acrylamides
Organic Letters ( IF 4.9 ) Pub Date : 2017-09-19 00:00:00 , DOI: 10.1021/acs.orglett.7b02384
Qun Zhao 1 , Thomas Poisson 1 , Xavier Pannecoucke 1 , Jean-Philippe Bouillon 1 , Tatiana Besset 1
Affiliation  

The Pd-catalyzed diastereoselective trifluoromethylthiolation of acrylamides was developed to allow the formation of the Z-isomer as a single product. Using a C–H bond functionalization strategy, the method was applied to a broad range of α-aryl, α-alkyl, and α,β-disubstituted acrylamides bearing the amide derived from the 8-aminoquinoline as a directing group. Mechanistic studies as well as postfunctionalization of the products were performed. This approach opens new routes to unprecedented SCF3-containing scaffolds.

中文翻译:

Pd催化官能化丙烯酰胺的非对映选择性三氟甲基硫醇化

开发了钯催化丙烯酰胺的非对映选择性三氟甲基硫醇化反应,以使Z-异构体形成单一产物。使用C–H键官能化策略,该方法适用于范围广泛的α-芳基,α-烷基和α,β-二取代的丙烯酰胺,这些酰胺带有衍生自8-氨基喹啉的酰胺作为导向基团。进行了机理研究以及产品的后功能化。这种方法为史无前例的含有SCF 3的支架开辟了新途径。
更新日期:2017-09-19
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