配体控制的涉及有机硅化合物的发散交叉偶联反应在硫醚和硫酯合成中的应用。
Ligand-Controlled Divergent Cross-Coupling Involving Organosilicon Compounds for Thioether and Thioester Synthesis.
机构信息
Shanghai Key Laboratory of Green Chemistry and Chemical Process, School of Chemistry and Molecular Engineering, East China Normal University , 3663N Zhongshan Road, Shanghai 200062, P. R. China.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Lu, Shanghai 200032, P. R. China.
出版信息
Org Lett. 2016 Apr 1;18(7):1550-3. doi: 10.1021/acs.orglett.6b00324. Epub 2016 Mar 14.
A divergent cross-coupling for both thioether and thioester construction from organosilicon compounds has been developed. Predominant selectivity for Hiyama-type coupling and C1 insertion reaction was achieved under the guidance of ligands. Thioether was obtained under ligand-free conditions in which disulfide generated from homocoupling could be prevented. Meanwhile, application of bidentate phosphine ligands under carbon monoxide atmosphere (CO balloon) afforded the thioester with little decomposition, which was revealed through interval NMR tracking.
一种从有机硅化合物出发构建硫醚和硫酯的发散交叉偶联反应已经被开发出来。在配体的引导下，主要选择性地发生了 Hiyama 型偶联和 C1 插入反应。在无配体条件下可以获得硫醚，其中可以防止由同种偶联生成的二硫醚。同时，在一氧化碳气氛（CO 气球）下使用双齿膦配体可以得到几乎没有分解的硫酯，通过间隔 NMR 跟踪可以揭示这一点。
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