Direct and Efficient C(sp3)-H Functionalization ofN-Acyl/Sulfonyl Tetrahydroisoquinolines (THIQs) With Electron-Rich Nucleophiles via 2,3-Dichloro-5,6-Dicyano-1,4-Benzoquinone (DDQ) Oxidation

被引：5
作者：
Yu, Heesun [1 ]
Kim, Hyoungsu [1 ]
Baek, Seung-Hoon [1 ]
Lee, Dongjoo [1 ]
机构：
[1] Ajou Univ, Coll Pharm, Res Inst Pharmaceut Sci & Technol RIPST, Suwon, South Korea
来源：
FRONTIERS IN CHEMISTRY | 2020年 / 8卷
关键词：
tetrahydroisoquinoline; oxidation; DDQ; electron-rich; natural products; DEHYDROGENATIVE COUPLING REACTIONS; C-H BONDS; TERTIARY-AMINES; MOLECULAR-OXYGEN; ANODIC CYANATION; N-BENZYL; MILD; ARYLATION; VANADIUM; DIVERSE;
D O I：
10.3389/fchem.2020.00629
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A highly efficient metal-free oxidative direct C(sp(3))-H functionalization ofN-acyl/sulfonyl 1,2,3,4-tetrahydroisoquinolines (THIQs) with a wide range of electron-rich nucleophiles was accomplished under mild conditions through oxidation with DDQ and subsequent trapping of the resulting reactive and stableN-acyl/sulfonyl iminium ions. The synthetic utility of this method was illustrated by a concise and efficient total synthesis of (+/-)-benzo[a]quinolizidine (10) in 3 steps from the knownN-Cbz 1,2,3,4-THIQ4b.
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页数：17
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