Copper-Catalyzed C(sp3)–S Bond and C(sp2)–S Bond Cross-Coupling of 2-(2-Iodobenzoyl) Substituted or 2-(2-Iodobenzyl) Substituted 1,2,3,4-Tetrahydroisoquinolines with Potassium Sulfide: Synthesis of Isoquinoline-Fused 1,3-Benzothiazine Scaffolds,The Journal of Organic Chemistry

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Copper-Catalyzed C(sp3)–S Bond and C(sp2)–S Bond Cross-Coupling of 2-(2-Iodobenzoyl) Substituted or 2-(2-Iodobenzyl) Substituted 1,2,3,4-Tetrahydroisoquinolines with Potassium Sulfide: Synthesis of Isoquinoline-Fused 1,3-Benzothiazine Scaffolds
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2017-02-01 00:00:00 , DOI: 10.1021/acs.joc.6b02943
Pan Dang ₁ , Zhilei Zheng ₁ , Yun Liang ₁

Affiliation

The sulfuration reaction of 2-(2-iodobenzoyl) substituted, or 2-(2-iodobenzyl) substituted 1,2,3,4-tetrahydroisoquinolines with potassium sulfide proceeded in the presence of copper catalysts to give tetrahydroisoquinoline-fused 1,3-benzothiazine scaffolds in moderate to appropriate yields. This protocol provided an efficient and simple strategy to construct the corresponding benzothiazine derivatives via formation of C(sp³)–S bond and C(sp²)–S bond, which the C–S bonds formed via different routes in this reaction (traditional cross-coupling reaction via the cleavage of C–I bond and oxidative cross-coupling reaction via C(sp³)–H bond functionalization).

中文翻译：

铜催化的2-（2-碘苯甲酰基）取代或2-（2-碘苄基）取代的1,2,3,4-四氢异喹啉的C（sp ³）-S键和C（sp ²）-S键铜偶联交联与硫化钾：异喹啉融合的1,3-苯并噻嗪支架的合成

在铜催化剂的存在下，进行2-（2-碘苯甲酰基）取代的或2-（2-碘苄基）取代的1,2,3,4-四氢异喹啉与硫化钾的硫化反应，得到四氢异喹啉稠合的1,3-苯并噻嗪支架的产率适中至适当。该协议提供了一种有效而简单的策略，即通过形成C（sp ³）–S键和C（sp ²）–S键来构建相应的苯并噻嗪衍生物，这些C–S键通过该反应中的不同途径形成（传统通过C–I键断裂进行的交叉偶联反应和通过C（sp ³）–H键官能化进行的氧化交叉偶联反应）。

更新日期：2017-02-01

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