Ni-Catalyzed Borylation of Aryl Fluorides via C-F Cleavage

被引：201

作者：

Liu, Xiang-Wei ^{[1
]}

Echavarren, Javier ^{[1
]}

Zarate, Cayetana ^{[1
]}

Martin, Ruben ^{[1
,2
]}

机构：

[1] ICIQ, Tarragona 43007, Spain

[2] Catalan Inst Res & Adv Studies ICREA, Barcelona 08010, Spain

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 39期

基金：

欧洲研究理事会;

关键词：

CROSS-COUPLING REACTIONS; ALKOXY DIBORON REAGENTS; O BOND-CLEAVAGE; GRIGNARD-REAGENTS; MEDICINAL CHEMISTRY; ROOM-TEMPERATURE; ORGANIC HALIDES; METHYL ETHERS; ACTIVATION; NICKEL;

D O I：

10.1021/jacs.5b08103

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A Ni-catalyzed borylation via C-F activation is described. This protocol is distinguished by a wide scope, including unactivated fluoroarenes, without compromising its efficiency and scalability, thus representing a significant step-forward toward the implementation of C-F activation protocols.

引用

收藏

页码：12470 / 12473

页数：4

相关论文

共 79 条

[1] Efficient aryl-(hetero)aryl coupling by activation of C-Cl and C-F bonds using nickel complexes of air-stable phosphine oxides [J].

Ackermann, L ;

Born, R ;

Spatz, JH ;

Meyer, D .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (44) :7216-7219

[2] 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

[3] CATALYTIC ACTIVATION OF CARBON-FLUORINE BONDS BY A SOLUBLE TRANSITION-METAL COMPLEX [J].

AIZENBERG, M ;

MILSTEIN, D .

SCIENCE, 1994, 265 (5170) :359-361

[4] Ni-Catalyzed Reduction of Inert C-O Bonds: A New Strategy for Using Aryl Ethers as Easily Removable Directing Groups [J].

Alvarez-Bercedo, Paula ;

Martin, Ruben .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (49) :17352-17353

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

Amii, Hideki ;

Uneyama, Kenji .

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

[6]

[Anonymous], 2015, OMCOS

[7] Rhodium-catalyzed substitution reaction of aryl fluorides with disulfides:: p-orientation in the polyarylthiolation of polyfluorobenzenes [J].

Arisawa, Mieko ;

Suzuki, Takaaki ;

Ishikawa, Tomofumi ;

Yamaguchi, Masahiko .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (37) :12214-+

[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] Efficient Synthesis of Aryl Boronates via Zinc-Catalyzed Cross-Coupling of Alkoxy Diboron Reagents with Aryl Halides at Room Temperature [J].

Bose, Shubhankar Kumar ;

Marder, Todd B. .

ORGANIC LETTERS, 2014, 16 (17) :4562-4565

← 1 2 3 4 5 6 7 8 →