Copper-Mediated N-Arylations of Hydantoins

被引：15

作者：

Thilmany, Pierre ^{[1
]}

Gerard, Phideline ^{[1
]}

Vanoost, Agathe ^{[2
]}

Deldaele, Christopher ^{[1
]}

Petit, Laurent ^{[2
]}

Evano, Gwilherm ^{[1
]}

机构：

[1] Univ Libre Bruxelles, Lab Chim Organ, Serv Chim & PhysicoChim Organ, Ave FD Roosevelt 50,CP160-06, B-1050 Brussels, Belgium

[2] Minakem Rech, 145 Chemin Lilas, F-59310 Beuvry La Foret, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 01期

关键词：

DERIVATIVES; ACID; 1,1-DIBROMO-1-ALKENES; ALKYNYLATION; GENERATION; INHIBITORS; ALKALOIDS; OXIDATION; COMPLEX;

D O I：

10.1021/acs.joc.8b02284

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A set of two broadly applicable procedures for the N-arylation of hydantoins is reported. The first one relies on the use of stoichiometric copper(I) oxide under ligand- and base-free conditions and enables a clean regioselective arylation at the N-3 nitrogen atom, while the second one is based on the use of catalytic copper(I) iodide and trans-N,N'-dimethylcyclohexane-1,2-diamine and promotes arylation at the N-1 nitrogen atom. Importantly, the combination of these two procedures affords a straightforward entry to diarylated hydantoins.

引用

页码：392 / 400

页数：9

共 50 条

[1] N-Arylations of Sulfoximines with 2-Arylpyridines by Copper-Mediated Dual N-H/C-H Activation
Wang, Long
Priebbenow, Daniel L.
Dong, Wanrong
Bolm, Carsten
ORGANIC LETTERS, 2014, 16 (10) : 2661 - 2663
[2] N-arylations with triphenylbismuthane.
Sorenson, RJ
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 218 : U173 - U173
[3] Efficient copper-promoted N-arylations of aryl halides with amines
Huang, He
Yan, Xiuhua
Zhu, Weiliang
Liu, Hong
Jiang, Hualiang
Chen, Kaixian
JOURNAL OF COMBINATORIAL CHEMISTRY, 2008, 10 (05): : 617 - 619
[4] New copper-mediated O-arylations of phenols with arylstannanes
Vakalopoulos, Alexandros
Kavazoudi, Xanthoula
Schoof, Joachim
TETRAHEDRON LETTERS, 2006, 47 (48) : 8607 - 8610
[5] Iron-catalyzed N-arylations of Amides
Correa, Arkaitz
Elmore, Simon
Bolm, Carsten
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (12) : 3527 - 3529
[6] A soluble base for the copper-catalyzed imidazole N-arylations with aryl halides
Liu, LB
Frohn, M
Xi, N
Dominguez, C
Hungate, R
Reider, PJ
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (24): : 10135 - 10138
[7] Copper-Catalyzed N-Arylations of Nitrogen-Containing Heterocycles in Water
Zhang, Jingxian
Yin, Huiqing
Han, Shiqing
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2012, 32 (08) : 1429 - 1433
[8] Copper-catalyzed N-arylations of small biomolecules with aryllead(IV) triacetates.
Konopelski, JP
Elliott, GI
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U98 - U98
[9] Transition-Metal-Free Intramolecular N-Arylations
Thome, Isabelle
Bolm, Carsten
ORGANIC LETTERS, 2012, 14 (07) : 1892 - 1895
[10] Active-copper-promoted expeditious N-arylations in aqueous media under microwave irradiation
Yadav, Lal Dhar S.
Yadav, Beerendra S.
Rai, Vijai K.
SYNTHESIS-STUTTGART, 2006, (11): : 1868 - 1872

← 1 2 3 4 5 →