Suzuki-Miyaura Coupling of Aryl Chlorides with Arylboronic Acids Using the Morpholine-NiCl2 Catalyst System

被引：4

作者：

Abe, Taichi ^{[1
]}

Mino, Takashi ^{[1
]}

Watanabe, Kohei ^{[1
]}

Sakamoto, Masami ^{[1
]}

机构：

[1] Chiba Univ, Dept Appl Chem & Biotechnol, Grad Sch Engn, Inage Ku, Chiba 2638522, Japan

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 31期

关键词：

Synthetic methods; C-C coupling; Cross coupling; Nickel; N ligands; NICKEL; HALIDES; CHLOROARENES; BIARYLS; ARENESULFONATES; PALLADIUM; MESYLATES;

D O I：

10.1002/ejoc.201402881

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report a new catalyst system, morpholine-NiCl2, for the Suzuki-Miyaura coupling of aryl chlorides with aryl-or alkenylboronic acids to give biaryl compounds. This catalyst system is easy to apply on a large scale because of its easy preparation and the use of inexpensive reagents. In addition, analysis of the residual nickel shows only 9.7 ppm remaining after normal work-up. This catalyst system has been applied to 26 compounds to give a variety of biaryl products, including hetero-biaryl compounds.

引用

页码：6983 / 6991

页数：9

共 48 条

[1] Suzuki-Miyaura Coupling of Aryl Sulfonates with Arylboronic Acids Using a Morpholine-Pd(OAc)2 Catalyst System [J].

Abe, Taichi ;

Mino, Takashi ;

Watanabe, Kohei ;

Yagishita, Fumitoshi ;

Sakamoto, Masami .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (18) :3909-3916

[2] Well-Defined Air-Stable Palladium HASPO Complexes for Efficient Kumada-Corriu Cross-Couplings of (Hetero)Aryl or Alkenyl Tosylates [J].

Ackermann, Lutz ;

Kapdi, Anant R. ;

Fenner, Sabine ;

Kornhaass, Christoph ;

Schulzke, Carola .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (10) :2965-2971

[3]

[Anonymous], ANGEW CHEM

[4]

[Anonymous], 2011, ANGEW CHEM

[5]

Asaumi T., 2009, WO Pat, Patent No. 2009136646

[6] A Versatile Catalyst System for Suzuki-Miyaura Cross-Coupling Reactions of C(sp2)-Tosylates and Mesylates [J].

Bhayana, Brijesh ;

Fors, Brett P. ;

Buchwald, Stephen L. .

ORGANIC LETTERS, 2009, 11 (17) :3954-3957

[7] Nickel(0) Complexes of Polyunsaturated Azamacrocyclic Ligands [J].

Brun, Sandra ;

Pla-Quintana, Anna ;

Roglans, Anna ;

Poerschke, Klaus-Richard ;

Goddard, Richard .

ORGANOMETALLICS, 2012, 31 (05) :1983-1990

[8] Traceless Solid-Phase Synthesis of Trifluoromethylarenes [J].

Doebele, Marion ;

Wiehn, Matthias S. ;

Braese, Stefan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (48) :11533-11535

[9] Development and Industrialization of Efficient Cross-Coupling Reactions [J].

Eguchi, Hisao ;

Nishiyama, Masakazu ;

Ishikawa, Shin-ichi ;

Soga, Shin-ichi ;

Koie, Yasuyuki .

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2012, 70 (09) :937-946

[10] Room-Temperature Nickel-Catalysed Suzuki-Miyaura Reactions of Aryl Sulfonates/Halides with Arylboronic Acids [J].

Fan, Xin-Heng ;

Yang, Lian-Ming .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (08) :1467-1471

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