Progress in the Synthesis of Hydrobenzofurans from O-Cyclohexadienone-tethered 1,6-Enynes

doi:10.6023/cjoc202105029

Abstract

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

Cite this article

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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Fig. & Tab. 24

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

Figure 2. Bioactive molecules containing hydrobenzofuran skeletons

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

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

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

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

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

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

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

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

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

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

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

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

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

Scheme 14. Cu catalyzed synthesis imide derived hydrobenzofurans

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

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

Scheme 17. Cu catalyzed synthesis allene derived hydrobenfurans

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

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

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

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

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

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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