Synthesis of selenated isochromenones by AgNO3-catalyzed three-component reaction of alkynylaryl esters, selenium powder and ArB(OH)2

被引：24

作者：

Jin, Guo-Qing ^{[1
]}

Gao, Wen-Xia ^{[1
]}

Zhou, Yun-Bing ^{[1
]}

Liu, Miao-Chang ^{[1
]}

Wu, Hua-Yue ^{[1
]}

机构：

[1] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China

来源：

RSC ADVANCES | 2020年 / 10卷 / 51期

基金：

中国国家自然科学基金;

关键词：

ALLYLIC ALCOHOLS; ORGANOSELENIUM; CYCLIZATION; OLEFINS; DISELENIDES; CONVERSION; OXIDATION; EPOXIDES; ROUTE;

D O I：

10.1039/d0ra06016j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reported is the AgNO3-catalyzed three-component reaction of alkynylaryl esters, selenium powder and ArB(OH)(2), providing a facile entry to selenated isochromenones. This work highlights the use of selenium powder as a selenium reagent in the synthesis of selenated isochromenones for the first time.

引用

页码：30439 / 30442

页数：4

共 39 条

[1] Selenium Radical Mediated Cascade Cyclization: Concise Synthesis of Selenated Benzofurans (Benzothiophenes) [J].

An, Cui ;

Li, Chen-Yuan ;

Huang, Xiao-Bo ;

Gao, Wen-Xia ;

Zhou, Yun-Bing ;

Liu, Miao-Chang ;

Wu, Hua-Yue .

ORGANIC LETTERS, 2019, 21 (17) :6710-6714

[2] Stereospecific total syntheses of sphingosine and its analogues from L-serine [J].

Azuma, H ;

Tamagaki, S ;

Ogino, K .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (11) :3538-3541

[3] Diselenides and allyl selenides as glutathione peroxidase mimetics.: Remarkable activity of cyclic seleninates produced in situ by the oxidation of allyl ω-hydroxyalkyl selenides [J].

Back, TG ;

Moussa, Z .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (44) :13455-13460

[4] Selenium-catalyzed oxidation of alkenes: insight into the mechanisms and developing trend [J].

Cao, Hongen ;

Qian, Rongrong ;

Yu, Lei .

CATALYSIS SCIENCE & TECHNOLOGY, 2020, 10 (10) :3113-3121

[5] Synthesis of selenium-doped carbon from glucose: An efficient antibacterial material against Xcc [J].

Cao, Hongen ;

Yang, Yufan ;

Chen, Xijun ;

Liu, Jian ;

Chen, Chao ;

Yuan, Shuzhong ;

Yu, Lei .

CHINESE CHEMICAL LETTERS, 2020, 31 (07) :1887-1889

[6] A cost-effective shortcut to prepare organoselenium catalysts via decarboxylative coupling of phenylacetic acid with elemental selenium [J].

Cao, Hongen ;

Liu, Mingxuan ;

Qian, Rongrong ;

Zhang, Xu ;

Yu, Lei .

APPLIED ORGANOMETALLIC CHEMISTRY, 2019, 33 (01)

[7] Energy saving and environment-friendly element-transfer reactions with industrial application potential [J].

Chen, Chao ;

Cao, Yitao ;

Wu, Xixi ;

Cai, Yuanli ;

Liu, Jian ;

Xu, Lin ;

Ding, Kehong ;

Yu, Lei .

CHINESE CHEMICAL LETTERS, 2020, 31 (05) :1078-1082

[8] Peptide Ligation at High Dilution via Reductive Diselenide-Selenoester Ligation [J].

Chisholm, Timothy S. ;

Kulkarni, Sameer S. ;

Hossain, Khondker R. ;

Cornelius, Flemming ;

Clarke, Ronald J. ;

Payne, Richard J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (02) :1090-1100

[9]

Dumont W., 1974, ANGEW CHEM, V86, P857

[10] A Metal-Free Route to Heterocyclic Trifluoromethyl- and Fluoroalkylselenolated Molecules [J].

Glenadel, Quentin ;

Ismalaj, Ermal ;

Billard, Thierry .

ORGANIC LETTERS, 2018, 20 (01) :56-59

← 1 2 3 4 →