Recent Progress in the Synthesis of Substituted Benzo[b]furan Derivatives

doi:10.6023/cjoc202110008

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (4): 945-964.DOI: 10.6023/cjoc202110008 Previous Articles Next Articles

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取代苯并[b]呋喃衍生物的合成研究进展

张志豪^a^,^b^,^c, 姜芯^a^,^b^,^c, 李清寒^a^,^b^,^c^,^*()

a 西南民族大学化学与环境学院成都 610041
b 西南民族大学化学与环境学院国家民委基础化学重点实验室成都 610041
c 西南民族大学化学与环境学院青藏高原污染控制化学与环境功能材料重点实验室成都 610041

收稿日期:2021-10-08 修回日期:2021-11-20 发布日期:2021-12-15
通讯作者: 李清寒
基金资助:
西南民族大学研究生创新基金(CX2020SZ18); 四川省科技支撑计划(2015NZ0033)

Recent Progress in the Synthesis of Substituted Benzo[b]furan Derivatives

Zhihao Zhang^a^,^b^,^c, Xin Jiang^a^,^b^,^c, Qinghan Li^a^,^b^,^c()

a College of Chemistry and Environment, Southwest Minzu University, Chengdu 610041
b Key Laboratory of General Chemistry of the National Ethnic Affairs Commission, College of Chemistry and Environment, Southwest Minzu University, Chengdu 610041
c Key Laboratory of pollution Control Chemistry and Environmental Functional Materials for Qinghai-Tibet Plateau of the National Ethnic Affairs Commission, College of Chemistry and Environment, Southwest Minzu University, Chengdu 610041

Received:2021-10-08 Revised:2021-11-20 Published:2021-12-15
Contact: Qinghan Li
Supported by:
Graduate Student Innovation Funds of Southwest Minzu University(CX2020SZ18); Sichuan Provincial Department of Science and Technology Support Program(2015NZ0033)

Benzo[b]furan structure is found in many natural products and bioactive compounds. Benzo[b]furan derivatives have attracted the attention of pharmaceutical chemists because of their antiviral, anticancer, insecticidal and anti inflammatory, analgesic and antioxidant activities. At present, many effective synthetic methods have been reported and become one of the hot topics of organic synthesis research in recent years. The research progress in the synthesis of substituted benzo[b]furan derivatives by cyclization or coupling reaction under the conditions of transition metal catalysis and catalysts free in recent ten years is reviewed.

Key words: benzo[b]furan, cross-coupling reaction, cyclization reaction, metal catalyst, catalyst free, research progress

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Zhihao Zhang, Xin Jiang, Qinghan Li. Recent Progress in the Synthesis of Substituted Benzo[b]furan Derivatives[J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 945-964.

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Fig. & Tab. 31

Scheme 1. Plausible mechanism of palladium catalyzed reaction of allylic esters with o-hydroxyhalobenzene to prepare substituted benzo[b]furans

Scheme 2. Plausible mechanism of reaction of 2-(1,1-dibromo- vinyl)phenol with phenyl(trialkoxy)silane to prepare substituted benzo[b]furan derivatives catalyzed by palladium

Scheme 3. Plausible mechanism of oxidative cyclization of phenol derivatives to prepare benzo[b]furan derivatives catalyzed by palladium

Scheme 4. Plausible mechanism of cyclization of o-chlorophenol and terminal alkynes to benzo[b]furan derivatives catalyzed by palladium

Scheme 5. Synthesis of benzo[b]furan derivatives with tricyclic structure

Scheme 6. Plausible mechanism of copper catalyzed cyclization of 2-(2,2-dibromovinyl)phenol with phenylacetylene to prepare substituted benzo[b]furan derivatives

Scheme 7. Plausible mechanism of one-pot synthesis of substituted benzo[b]furan derivatives from acyl chloride, phosphine ylide reagent and o-iodophenol catalyzed by copper

Scheme 8. Possible mechanism of synthesis of benzo[b]furan rings from calcium carbide

Scheme 9. Plausible mechanism of synthesis of substituted benzo[b]furans from 2-haloarylaldehydes and 2-hydroxyphenylacetocyanide catalyzed by copper

Scheme 10. Plausible mechanism of intramolecular cyclization of 2-(2-iodophenoxy)-1-arylketone to benzo[b]furan derivatives catalyzed by nickel

Scheme 11. Plausible mechanism of cycloisomerization of 2-(iodoacetyl)-aryl esters to prepare substituted benzo[b]furan derivatives catalyzed by gold

Scheme 12. Plausible mechanism for the synthesis of substituted benzo[b]furan derivatives by the cyclization of 2-hydroxy- phenylalkyne compounds with N-pivaloyloxy amides catalyzed by rhodium

Scheme 13. Plausible mechanism of cyclization of salicylaldehyde and diazo compounds to synthesize substituted benzo[b]furan derivatives catalyzed by rhodium

Scheme 14. Plausible mechanism of hydrogen transfer reaction of benzyl alcohol to synthesize substituted benzo[b]furan derivatives catalyzed by iridium

Scheme 15. Plausible mechanism of intramolecular cyclization of o-alkynylphenol to prepare substituted benzo[b]furans catalyzed by indium

Scheme 16. Plausible mechanism of reaction of aromatic ketones with 1,4-benzoquinone to synthesize substituted benzo[b]furan derivatives catalyzed by scandium

Scheme 17. Plausible mechanism of O-arylhydroxylamine reacting with ketone to prepare substituted benzo[b]furan derivatives in the presence of methanesulfonic acid

Scheme 18. Plausible mechanism of synthesis of substituted benzo[b]furan derivatives by the reaction of o-hydroxybenzoate with 1,1-dichloroethylene in the presence of alkali

Scheme 19. Benzo[b]furan-2-carboxamides from ortho-acetylphenols and 2-chloroacetamides

Scheme 20. Synthesis of 2-substitute benzofurans

Scheme 21. Plausible mechanism of preparation of substituted benzo[b]furan derivatives by the reaction of trifluoromethanesulfonic acid (2-trimethylsilyl)phenyl ester with thioylide in the presence of cesium fluoride

Scheme 22. Plausible mechanism of synthesis of substituted benzo[b]furan derivatives by the reaction of enals with 2-halophenol in the presence of K2CO3

Scheme 24. Plausible mechanism of synthesis of substituted benzo[b]furan derivatives by the reaction of nitroepoxide and salicylaldehyde in the presence of alkali

Scheme 24. Plausible mechanism of preparation of substituted benzo[b]furan derivatives by the cyclization of o-hydroxystyrene derivatives in the presence of iodobenzene acetate

Scheme 25. Plausible mechanism of preparation of substituted benzo[b]furans by the cyclization of o-hydroxystyrene derivatives in the presence of iodobenzene acetate

Scheme 26. Plausible mechanism of preparation of benzo[b]furan derivatives by the reaction of 1-(2-hydroxyphenyl)-2-chloroethanone with Grignard reagent

Scheme 27. Plausible mechanism of reaction of benzo[b]furan with arylimidazole borate to prepare benzo[b]furan derivatives catalyzed by palladium

Scheme 28. Plausible mechanism of coupling reaction of organoaluminum reagent with 2-halobenzo[b]furan to prepare 2- substituted benzo[b]furan derivatives by palladium catalyzed

Scheme 29. Plausible mechanism of reaction of benzo[b]furan with iodobenzene derivatives to prepare 2-substituted benzo[b]- furan catalyzed by palladium

Scheme 31. Synthesis of 2-substituted benzo[b]furan derivatives by copper catalyzed reaction of benzofuran with o-benzoyl hydroxylamine

Scheme 31. Plausible mechanism of synthesis of 2-substituted benzo[b]furan derivatives from 3-iodothrone and benzo[b]furan by photocatalytic

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取代苯并[b]呋喃衍生物的合成研究进展

Recent Progress in the Synthesis of Substituted Benzo[b]furan Derivatives

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