亲电三氟甲基硫代化/半频哪醇重排：制备具有α-季碳中心的β-SCF 羰基化合物。
Electrophilic Trifluoromethylthiolation/Semipinacol Rearrangement: Preparation of β-SCF Carbonyl Compounds with α-Quaternary Carbon Center.
机构信息
State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering , Lanzhou University , Lanzhou 730000 , P. R. China.
School of Chemistry and Chemical Engineering, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs , Shanghai Jiao Tong University , 800 Dongchuan Road , Shanghai 200240 , P. R. China.
出版信息
Org Lett. 2018 Jul 20;20(14):4227-4230. doi: 10.1021/acs.orglett.8b01627. Epub 2018 Jul 3.
A new and modular electrophilic trifluoromethylthiolation/semipinacol rearrangement of allylic silyl ethers has been developed under mild conditions. This approach allows the formation of a number of β-SCF carbonyl compounds with a cyclic and all-carbon quaternary center framework in moderate to good yields. It should be noted that this achievement is a metal-free process and just requires the use of simple acetyl chloride as an acidic promoter. Additionally, an interesting H-migration in competition with aryl-migration process was revealed.
一种新的、模块化的亲电性三氟甲基硫代化/半频哪醇重排反应已被开发出来，可在温和条件下应用于烯丙基硅醚。该方法可以在中等至良好的产率下形成多种β-SCF 羰基化合物，具有环状和全碳季碳中心骨架。值得注意的是，这一成就实现了无金属过程，仅需要使用简单的乙酰氯作为酸性促进剂。此外，还揭示了与芳基迁移过程竞争的有趣的 H-迁移。
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