Nickel-Catalyzed Decarbonylative Cycloaddition of Benzofuran-2,3-diones with Alkynes to Flavones

被引：8

作者：

Zhang, Yu-Yang ^{[1
]}

Li, Han ^{[1
]}

Jiang, Xiaoding ^{[1
]}

Reddy, Chitreddy V. Subba ^{[1
]}

Liang, Hao ^{[1
]}

Zhang, Yaqi ^{[1
]}

Cao, Rihui ^{[1
]}

Sun, Raymond Wai-Yin ^{[2
]}

Tse, Man Kin ^{[2
]}

Qiu, Liqin ^{[1
]}

机构：

[1] Sun Yat Sen Univ, Key Lab Low Carbon Chem & Energy Conservat Guangd, Sch Chem, Guangzhou 510006, Peoples R China

[2] Guangzhou Lee & Man Technol Co Ltd, 8 Huanshi Ave South, Guangzhou 511458, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2022年 / 364卷 / 03期

关键词：

Benzofuran-2; 3-diones; Alkynes; Flavones; Decarbonylative cycloaddition; Nickel catalysis; C-H ACTIVATION; BAKER-VENKATARAMAN REARRANGEMENT; PLANT FLAVONOIDS; BOND-CLEAVAGE; PALLADIUM; ANNULATION; CHROMONES; SALICYLALDEHYDES; ESTERS; HYDRIDE;

D O I：

10.1002/adsc.202101241

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Y Using dppe as the ligand, the Nickel-catalyzed decarbonylative cycloaddition of benzofuran-2,3-diones with alkynes was established, and a variety of functional flavones were synthesized in 65-99% yields. Terminal alkynes with substituted phenyl groups and internal alkynes such as aryl acyl acetylenes and diphenylacetylenes are suitable for this reaction. The effects of bases on the reactions of different types of alkyne substrates were also investigated and discussed.

引用

页码：525 / 530

页数：6

共 68 条

[1] Acylated flavone C-glycosides from Cucumis sativus
Abou-Zaid, MM
Lombardo, DA
Kite, GC
Grayer, RJ
Veitch, NC
[J]. PHYTOCHEMISTRY, 2001, 58 (01) : 167 - 172
[2] An accessible derivatives of chromonol
Allan, J
Robinson, R
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1924, 125 : 2192 - 2195
[3] Decarbonylative C-H Coupling of Azoles and Aryl Esters: Unprecedented Nickel Catalysis and Application to the Synthesis of Muscoride A
Amaike, Kazuma
Muto, Kei
Yamaguchi, Junichiro
Itami, Kenichiro
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) : 13573 - 13576
[4] [Anonymous], 2012, ANGEW CHEM, V124, P11495
[5] Access to Flavones via a Microwave-Assisted, One-Pot Sonogashira-Carbonylation-Annulation Reaction
Awuah, Emelia
Capretta, Alfredo
[J]. ORGANIC LETTERS, 2009, 11 (15) : 3210 - 3213
[6] Molecular rearrangement of some o-acyloxyacetophenones and the mechanism of the production of 3-acylchromones
Baker, W
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1933, : 1381 - 1389
[7] Ru(II)-Catalyzed C-H activation and annulation of salicylaldehydes with monosubstituted and disubstituted alkynes
Baruah, Swagata
Kaishap, Partha Pratim
Gogoi, Sanjib
[J]. CHEMICAL COMMUNICATIONS, 2016, 52 (88) : 13004 - 13007
[8] Free-energy relationships between the proton and hydride donor abilities of [HNi(diphosphine)2]+ complexes and the half-wave potentials of their conjugate bases
Berning, DE
Miedaner, A
Curtis, CJ
Noll, BC
DuBois, MCR
Dubois, DL
[J]. ORGANOMETALLICS, 2001, 20 (09) : 1832 - 1839
[9] Relative hydride, proton, and hydrogen atom transfer abilities of [HM(diphosphine)2]PF6 complexes (M = Pt, Ni)
Berning, DE
Noll, BC
DuBois, DL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (49) : 11432 - 11447
[10] Dietary agents in cancer prevention: flavonoids and isoflavonoids
Birt, DF
Hendrich, S
Wang, WQ
[J]. PHARMACOLOGY & THERAPEUTICS, 2001, 90 (2-3) : 157 - 177

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