Palladium-Catalyzed Synthesis of α-Diimines from Triarylbismuthines and Isocyanides

被引：50

作者：

Kobiki, Yohsuke ^{[1
]}

Kawaguchi, Shin-ichi ^{[1
]}

Ogawa, Akiya ^{[1
]}

机构：

[1] Osaka Prefecture Univ, Dept Appl Chem, Grad Sch Engn, Naka Ku, Sakai, Osaka 5998531, Japan

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 14期

关键词：

CROSS-COUPLING REACTION; MULTICOMPONENT REACTIONS; ORGANOBISMUTH REAGENTS; DOUBLE INSERTION; C-H; COMPLEXES; ARYLATION; ALKYNES; BOND; ISONITRILE;

D O I：

10.1021/acs.orglett.5b01566

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this study, we report a highly selective coupling reaction between triarylbismuthines and isocyanides using palladium diacetate as the catalyst, affording alpha-diimines, with the formation of three C-C bonds. Among several aryl sources,(Ar-YLn : Y = B, Sn, Pb, Sb, Bi, I), only triarylbismuthines successfully undergo coupling with isocyanides to selectively afford alpha-diimines. The coupling reaction exhibits the advantages of high atom economy and convenient operation, with no need for any additive.

引用

页码：3490 / 3493

页数：4

共 45 条

[1]

Akritopoulou-Zanze I., 2005, CURR OPIN CHEM BIOL, V7, P218

[2] Recent advances in the development and applications of post-Ugi transformations [J].

Akritopoulou-Zanze, Irini ;

Djuric, Stevan W. .

HETEROCYCLES, 2007, 73 (01) :125-+

[3] METALLIC COPPER CATALYSIS OF N-ARYLATION OF AMINES BY TRIARYLBISMUTH DIACYLATES [J].

BARTON, DHR ;

FINET, JP ;

KHAMSI, J .

TETRAHEDRON LETTERS, 1986, 27 (31) :3615-3618

[4] Metal-Mediated and Metal-Catalyzed Reactions of Isocyanides [J].

Boyarskiy, Vadim P. ;

Bokach, Nadezhda A. ;

Luzyanin, Konstantin V. ;

Kukushkin, Vadim Yu .

CHEMICAL REVIEWS, 2015, 115 (07) :2698-2779

[5] Allylic: Amination of cyclohexene catalyzed by ruthenium complexes. A new reaction involving an intermolecular C-H functionalization [J].

Cenini, S ;

Ragaini, F ;

Tollari, S ;

Paone, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (47) :11964-11965

[6]

Chatani N., 1991, CHEM EXP, V6, P339

[7] RHODIUM(I)-CATALYZED AND PALLADIUM(0)-CATALYZED CARBONYLATION OF TRIARYLBISMUTHINES WITH CARBON-MONOXIDE VIA A POSSIBLE OXIDATIVE ADDITION OF A CARBON BISMUTH BOND TO RHODIUM(I) AND PALLADIUM(0) [J].

CHO, CS ;

YOSHIMORI, Y ;

UEMURA, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1995, 68 (03) :950-957

[8] REACTIONS OF PALLADIUM(II)-ISOCYANIDE COMPLEXES WITH PHENYL DERIVATIVES OF HEAVY METALS [J].

CROCIANI, B ;

NICOLINI, M ;

BOSCHI, T .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1971, 33 (03) :C81-&

[9] Recent developments in isocyanide based multicomponent reactions in applied chemistry [J].

Dömling, A .

CHEMICAL REVIEWS, 2006, 106 (01) :17-89

[10]

Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO

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