Nickel-catalyzed amination of aryl fluorides with primary amines

被引：42

作者：

Harada, Tomoya ^{[1
]}

Ueda, Yusuke ^{[1
]}

Iwai, Tomohiro ^{[1
]}

Sawamura, Masaya ^{[1
]}

机构：

[1] Hokkaido Univ, Fac Sci, Dept Chem, Sapporo, Hokkaido 0600810, Japan

来源：

CHEMICAL COMMUNICATIONS | 2018年 / 54卷 / 14期

关键词：

C-F BOND; ALKYL GRIGNARD-REAGENTS; ORGANOZINC REAGENTS; MEDICINAL CHEMISTRY; MECHANISTIC ASPECTS; ACTIVATION; FLUOROARENES; COMPLEXES; CLEAVAGE; FLUOROBENZENES;

D O I：

10.1039/c7cc08181b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The Ni-catalyzed cross-coupling reaction between aryl fluorides and primary amines was enabled by the 1,2-bis(dicyclohexyl-phosphino) benzene (DCYPBz) or 1,2-bis(dicyclohexylphosphino) ethane (DCYPE) ligands. Both N-alkyl- and N-aryl-substituted primary amines participated in the selective reaction to form secondary amines. This protocol would potentially be useful for late-stage diversification of fluorinated compounds with complex structures for the synthesis of functionally interesting aniline derivatives.

引用

页码：1718 / 1721

页数：4

共 47 条

[1] Functionalization of Fluorinated Molecules by Transition-Metal-Mediated C-F Bond Activation To Access Fluorinated Building Blocks [J].

Ahrens, Theresia ;

Kohlmann, Johannes ;

Ahrens, Mike ;

Braun, Thomas .

CHEMICAL REVIEWS, 2015, 115 (02) :931-972

[2] C-F Bond Activation in Organic Synthesis [J].

Amii, Hideki ;

Uneyama, Kenji .

CHEMICAL REVIEWS, 2009, 109 (05) :2119-2183

[3] Nickel: The "Spirited Horse" of Transition Metal Catalysis [J].

Ananikov, Valentine P. .

ACS CATALYSIS, 2015, 5 (03) :1964-1971

[4]

[Anonymous], 2004, Metal-Catalyzed Cross-Coupling Reactions

[5] On the Catalytic Hydrodefluorination of Fluoroaromatics Using Nickel Complexes: The True Role of the Phosphine [J].

Arevalo, Alma ;

Tlahuext-Aca, Adrian ;

Flores-Alamo, Marcos ;

Garcia, Juventino J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (12) :4634-4639

[6] Oxidative Addition of Aryl Electrophiles to a Prototypical Nickel(0) Complex: Mechanism and Structure/Reactivity Relationships [J].

Bajo, Sonia ;

Laidlaw, Gillian ;

Kennedy, Alan R. ;

Sproules, Stephen ;

Nelson, David J. .

ORGANOMETALLICS, 2017, 36 (08) :1662-1672

[7] Bond dissociation energies of organic molecules [J].

Blanksby, SJ ;

Ellison, GB .

ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (04) :255-263

[8] Fluorine in medicinal chemistry [J].

Böhm, HJ ;

Banner, D ;

Bendels, S ;

Kansy, M ;

Kuhn, B ;

Müller, K ;

Obst-Sander, U ;

Stahl, M .

CHEMBIOCHEM, 2004, 5 (05) :637-643

[9]

Böhm VPW, 2001, ANGEW CHEM INT EDIT, V40, P3387

[10] AROMATIC NUCLEOPHILIC SUBSTITUTION REACTIONS [J].

BUNNETT, JF ;

ZAHLER, RE .

CHEMICAL REVIEWS, 1951, 49 (02) :273-412

← 1 2 3 4 5 →