Desulfitative palladium-catalyzed direct C-3 arylation of indolizines with arylsulfonyl chlorides

被引：21

作者：

Zhang, Wei ^{[1
]}

Liu, Fang ^{[2
]}

Zhao, Baoli ^{[3
,4
]}

机构：

[1] Xinxiang Univ, Dept Chem & Chem Engn, Xinxiang 453003, Henan Province, Peoples R China

[2] Hebei North Univ, Life Sci Res Ctr, Zhangjiakou, Hebei Province, Peoples R China

[3] Shaoxing Univ, Inst Appl Chem, Shaoxing 312000, Zhejiang, Peoples R China

[4] Shaoxing Univ, Dept Chem, Shaoxing 312000, Zhejiang, Peoples R China

来源：

APPLIED ORGANOMETALLIC CHEMISTRY | 2015年 / 29卷 / 08期

基金：

中国国家自然科学基金;

关键词：

desulfitative arylation; indolizines; arylsulfonyl chlorides; C-H BOND; ALTERNATIVE COUPLING PARTNERS; SULFONYL CHLORIDES; CROSS-COUPLINGS; BENZENESULFONYL CHLORIDES; ARENESULFONYL CHLORIDES; ARYLBORONIC ACIDS; ROOM-TEMPERATURE; TERMINAL ALKYNES; ARYL BROMIDES;

D O I：

10.1002/aoc.3326

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An efficient Pd-catalyzed desulfitative approach to C-3 arylation of indolizine derivatives has been developed, and the protocol uses readily available arylsulfonyl chlorides as the arylation reagent under nitrogen. This transformation was performed in a mixed solvent of 1-methyl-2-pyrrolidone and dimethoxyethane using simple triphenylphosphine as a ligand, which provides a new method for the C-3 arylation of indolizines. Copyright (c) 2015 John Wiley & Sons, Ltd.

引用

页码：524 / 527

页数：4

共 63 条

[1] Synthesis and characterization of a substituted indolizine and investigation of its photoluminescence quenching via electron-deficient nitroaromatics [J].

Bayazit, Mustafa K. ;

Coleman, Karl S. .

ARKIVOC, 2014, :362-371

[2] Benzenesulfonyl Chlorides: Alternative Coupling Partners for Regiocontrolled Palladium-Catalyzed Direct Desulfitative 5-Arylation of Furans [J].

Beladhria, Anissa ;

Yuan, Kedong ;

Ben Ammar, Hamed ;

Soule, Jean-Francois ;

Ben Salem, Ridha ;

Doucet, Henri .

SYNTHESIS-STUTTGART, 2014, 46 (18) :2515-2523

[3]

Böhm VPW, 2000, EUR J ORG CHEM, V2000, P3679, DOI 10.1002/1099-0690(200011)2000:22<3679::AID-EJOC3679>3.0.CO

[4]

2-X

[5]

Boot A, 2014, ANTICANCER RES, V34, P1673

[6] 7,8,9,10-Tetrahydropyrrolo[2,1-a]isoquinolines in the search for new indolizine derivatives [J].

Caira, Mino R. ;

Popa, Marcel Mire ;

Draghici, Constantin ;

Barbu, Loredana ;

Dumitrescu, Denisa ;

Dumitrascu, Florea .

TETRAHEDRON LETTERS, 2014, 55 (41) :5635-5638

[7] Palladium-catalyzed desulfitative C-H arylation of azoles with sodium sulfinates [J].

Chen, Ru ;

Liu, Saiwen ;

Liu, Xinhua ;

Yang, Luo ;

Deng, Guo-Jun .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (22) :7675-7679

[8] Palladium-catalyzed desulfitative cross-coupling of arylsulfinates with arylboronic acids [J].

Cheng, Kai ;

Yu, Hai-Zhu ;

Zhao, Baoli ;

Hu, Sai ;

Zhang, Xian-Man ;

Qi, Chenze .

RSC ADVANCES, 2014, 4 (101) :57923-57928

[9] Palladium-Catalyzed Hiyama-Type Cross-Coupling Reactions of Arenesulfinates with Organosilanes [J].

Cheng, Kai ;

Hu, Sai ;

Zhao, Baoli ;

Zhang, Xian-Man ;

Qi, Chenze .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (10) :5022-5025

[10] Cascade carbopalladation-annulation approach toward polycylic derivatives of indole and indolizine [J].

Chernyak, Natalia ;

Tilly, David ;

Li, Zhou ;

Gevorgyan, Vladimir .

ARKIVOC, 2011, :76-91

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