基于O-环己二烯酮型1,6-烯炔合成氢化苯并呋喃的反应研究进展

doi:10.6023/cjoc202105029

摘要/Abstract

氢化苯并呋喃骨架广泛存在于生物活性分子、天然产物和药物分子中, 过渡金属催化的O-环己二烯酮型1,6-烯炔经分子内或分子间C—H键官能团化/环化串联反应是构建这类骨架较为经济、有效的方法. 总结了过渡金属催化O-环己二烯酮型1,6-烯炔经C—H键官能团化/环化串联反应合成氢化苯并呋喃类化合物反应的研究进展, 主要介绍了各类过渡金属催化的反应类型、反应机理和手性控制中配体的选择, 并对该领域所面临的挑战和发展前景进行了展望与探讨.

关键词: O-环己二烯酮型1,6-烯炔, 环化反应, C—H键官能团化, 氢化苯并呋喃

Hydrobenzofurans are abundant in bioactive molecules, natural products and drug molecules. Transition-metal- catalyzed intramolecular or intermolecular C—H bond functionalization/cyclization cascade of O-linkered cyclohexadienone-tethered 1,6-enynes is an economic and efficient way to construct this skeleton. The progress in the synthesis of hydrobenzofurans from cyclohexadienone-tethered 1,6-enynes via C—H bond functionalization/cyclization cascade catalyzed by different transition-metals is discussed. The relevant reaction modes, mechanisms and the selection of ligands for chiral control are mainly introduced. Finally, the challenges and development prospects in this field are also prospected and discussed.

Key words: O-cyclohexadienone-tethered 1,6-enyne, cyclization reaction, C—H bond functionalization, hydrobenzofuran

引用此文

李志清, 邱潇杨, 孟楠, 柳竹青. 基于O-环己二烯酮型1,6-烯炔合成氢化苯并呋喃的反应研究进展[J]. 有机化学, 2021, 41(11): 4306-4319.

Zhiqing Li, Xiaoyang Qiu, Nan Meng, Zhuqing Liu. Progress in the Synthesis of Hydrobenzofurans from O-Cyclohexadienone-tethered 1,6-Enynes[J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4306-4319.

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图/表 24

图1. 环己二烯酮型1,6-烯炔的多反应性

Figure 1. Reactivity of O-linkered cyclohexadienone-tethered 1,6-enynes

图2. 含氢化苯并呋喃骨架的生物活性分子

Figure 2. Bioactive molecules containing hydrobenzofuran skeletons

图式1. 环己二烯酮型1,6-烯炔环化反应主要反应路径

Scheme 1. Main pathway of cyclization of cyclohexadienone- tethered 1,6-enynes

图式2. Pd催化环己二烯酮型1,6-烯炔酯化/环化反应

Scheme 2. Pd catalyzed acetoxylation/cyclization of cyclohexadienone-tethered 1,6-enynes

图式3. Pd催化环己二烯酮型1,6-烯炔芳基化/环化反应

Scheme 3. Pd catalyzed arylation/cyclization of cyclohexadienone-tethered 1,6-enynes

图式4. 环己二烯酮型1,6-烯炔双酯化/环化反应

Scheme 4. Diacetoxylation/cyclization of cyclohexadienone- tethered 1,6-enynes

图式5. Rh催化环己二烯酮型1,6-烯炔不对称芳基化/环化反应

Scheme 5. Rh catalyzed asymmetric arylation/cyclization of cyclohexadienone-tethered 1,6-enynes

图式6. Rh催化环己二烯酮型1,6-烯炔芳基化/环化反应机理

Scheme 6. Reaction mechanism of Rh catalyzed arylation/ cyclization of cyclohexadienone-tethered 1,6-enynes

图式7. 苯甲酰胺导向环己二烯酮型1,6-烯炔芳基化/环化反应

Scheme 7. Benzamide directed arylation/cyclization of cyclohexadienone-tethered 1,6-enynes

图式8. 嘧啶导向环己二烯酮型1,6-烯炔芳基化/环化反应

Scheme 8. Pyrimidine directed arylation/cyclization of cyclohexadienone-tethered 1,6-enynes

图式9. Rh催化环己二烯酮型1,6-烯炔还原环化反应

Scheme 9. Rh catalyzed reductive cyclization of cyclohexadienone-tethered 1,6-enynes

图式10. 铑催化环己二烯酮型1,6-烯炔炔基化/环化反应

Scheme 10. Rh catalyzed alkynylation/cyclization of cyclohexadienone-tethered 1,6-enynes

图式11. 环己二烯酮型1,6-烯炔不对称氧化/环化反应

Scheme 11. Asymmetric oxidation/cyclization of cyclohexadienone-tethered 1,6-enynes

图式12. 环己二烯酮型1,6-烯炔烯基化/环化反应

Scheme 12. Alkenylation/cyclization of cyclohexadienone- tethered 1,6-enynes

图式13. Cu催化环己二烯酮型1,6-烯炔硼化/环化反应

Scheme 13. Cu catalyzed boronation/cyclization of cyclohexadienone-tethered 1,6-enynes

图式14. Cu催化亚胺酯衍生化的氢化苯并呋喃化合物的合成

Scheme 14. Cu catalyzed synthesis imide derived hydrobenzofurans

图式15. Cu催化环己二烯酮型1,6-烯炔三组分反应

Scheme 15. Cu catalyzed three-component reaction of cyclohexadienone-tethered 1,6-enynes

图式16. 环己二烯酮型1,6-烯炔Kinagasa/Michael加成反应

Scheme 16. Kinagasa/Michael addition of cyclohexadienone- tethered 1,6-enynes

图式17. Cu催化联烯衍生化的氢化苯并呋喃化合物的合成

Scheme 17. Cu catalyzed synthesis allene derived hydrobenfurans

图式18. Au催化环己二烯酮型1,6-烯炔环化反应

Scheme 18. Cyclization of cyclohexadienone-tethered 1,6-enynes catalyzed by Au

图式19. 环己二烯酮型1,6-烯炔环丙烷化/环化反应

Scheme 19. Cyclopropanation/cyclization of cyclohexadienone- tethered 1,6-enynes

图式20. Mn催化环己二烯酮型1,6-烯炔芳基化/环化反应

Scheme 20. Mn catalyzed arylation/cyclization of cyclohexadienone-tethered 1,6-enynes

图式21. Ni催化环己二烯酮型1,6-烯炔环化反应

Scheme 21. Ni catalyzed cyclization of cyclohexadienone-tethered 1,6-enynes

图式22. Fe催化环己二烯酮型1,6-烯炔环化反应

Scheme 22. Fe catalyzed cyclization of cyclohexadenone-tethered 1,6-enynes

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