Palladium-Catalyzed N-Arylation of Sulfoximines with Aryl Sulfonates

被引：28

作者：

Yang, Qingjing ^{[1
]}

Choy, Pui Ying ^{[2
]}

Zhao, Qingyang ^{[2
]}

Leung, Man Pan ^{[2
]}

Chan, Hoi Shan ^{[2
]}

So, Chau Ming ^{[1
]}

Wong, Wing-Tak ^{[1
]}

Kwong, Fuk Yee ^{[1
,2
]}

机构：

[1] Hong Kong Polytech Univ, Shenzhen Res Inst SZRI, Shenzhen 518057, Peoples R China

[2] Chinese Univ Hong Kong, Dept Chem, Shatin, Hong Kong, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 18期

基金：

中国国家自然科学基金;

关键词：

MEDICINAL CHEMISTRY; BOND ACTIVATION; ONE-POT; MESYLATES; LIGANDS; IODIDES; AMINATION; CHLORIDES; BROMIDES; TOSYLATES;

D O I：

10.1021/acs.joc.8b01599

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium-catalyzed C-N bond coupling reaction between NH-sulfoximines and aryl halides (e.g., -Br, -I, and -CI and pseudohalides -OTf and -ONf) was successfully achieved. Nevertheless, aryl tosylates/mesylates left much to be achieved. In this report, a general N-arylation of sulfoximines with aryl sulfonates is described. Using Pd(OAc)(2)/MeO-CM-phos complex, the N-aryl sulfoximine products can be obtained in good-to-excellent yields (up to 99%) with good common functional group compatibility. In addition to arene moieties, alkenyl tosylates are shown to be successful coupling partners.

引用

页码：11369 / 11376

页数：8

共 50 条

[1] Palladium-catalyzed N-arylation of sulfoximines with aryl bromides and aryl iodides
Bolm, C
Hildebrand, JP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (01): : 169 - 175
[2] Efficient palladium-catalyzed N-arylation of a sulfoximine with aryl chlorides
Yongpruksa, Nattawut
Calkins, Nathan L.
Harmata, Michael
[J]. CHEMICAL COMMUNICATIONS, 2011, 47 (27) : 7665 - 7667
[3] Palladium-catalyzed α-arylation of sulfoximines
Cho, GY
Bolm, C
[J]. ORGANIC LETTERS, 2005, 7 (07) : 1351 - 1354
[4] Palladium-Catalyzed N-Arylation of Cyclopropylamines
Gildner, Peter G.
DeAngelis, Andrew
Colacot, Thomas J.
[J]. ORGANIC LETTERS, 2016, 18 (06) : 1442 - 1445
[5] Palladium-catalyzed N-arylation of N,N-dialkylhydrazines with aryl chlorides
Cacchi, Sandro
Fabrizi, Giancarlo
Goggiamani, Antonella
Sgalla, Simona
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (03) : 453 - 458
[6] Efficient palladium-catalyzed N-arylation of indoles
Old, DW
Harris, MC
Buchwald, SL
[J]. ORGANIC LETTERS, 2000, 2 (10) : 1403 - 1406
[7] Palladium-catalyzed intramolecular α-arylation of sulfoximines
Bolm, C
Okamura, H
Verrucci, M
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 687 (02) : 444 - 450
[8] Palladium-Catalyzed N-Arylation of Iminodibenzyls and Iminostilbenes with Aryl-and Heteroaryl Halides
Huang, Wenliang
Buchwald, Stephen L.
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (40) : 14186 - 14189
[9] Palladium-Catalyzed N-Arylation of Amines and Amides with Aryltrimethylgermanes
Zhang, Qiang
Liu, Cunfang
Shi, Juan
Xu, Qiong
Jin, Lingxia
Zhao, Chaibin
Zhang, Tianlei
[J]. SYNLETT, 2016, 27 (13) : 1945 - 1948
[10] Efficient copper-catalyzed N-arylation of sulfoximines with aryl iodides and aryl bromides
Sedelmeier, J
Bolm, C
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (17): : 6904 - 6906

← 1 2 3 4 5 →