N-Heterocyclic Carbene Derived Nickel-Pincer Complexes: Efficient and Applicable Catalysts for Suzuki-Miyaura Coupling Reactions of Aryl/Alkenyl Tosylates and Mesylates

被引：138

作者：

Kuroda, Jun-ichi ^{[1
]}

Inamoto, Kiyofumi ^{[1
]}

Hiroya, Kou ^{[1
]}

Doi, Takayuki ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Aoba Ku, Sendai, Miyagi 9808578, Japan

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 2009卷 / 14期

关键词：

Carbene ligands; Pincer complexes; Cross-coupling; Nickel; ARYL TOSYLATES; CROSS-COUPLINGS; ARYLBORONIC ACIDS; ALKENYL TOSYLATES; 4-SUBSTITUTED COUMARINS; VINYL TOSYLATES; SOLID-PHASE; PALLADIUM; ARENESULFONATES; ACTIVATION;

D O I：

10.1002/ejoc.200900067

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Catalytic activities of NHC-derived nickel-pincer complexes for the Suzuki-Miyaura coupling reactions of aryl/alkenyl to-sylates and mesylates are described. In the presence of a catalytic amount of nickelacycle 1a, a wide array of tosylates and mesylates reacted with several aryl- and alkenylboronic acids to afford the coupling products, generally in high yields. Fine tuning of the reaction conditions for each class of electrophiles was achieved only by choosing the appropriate reaction medium (DME for tosylates, dioxane for mesylates). ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

引用

页码：2251 / 2261

页数：11

共 87 条

[81] Highly efficient cyclopalladated ferrocenylimine catalyst for Suzuki cross-coupling reaction of 3-pyridylboronic pinacol ester with aryl halides [J].

Zhang, JL ;

Zhao, L ;

Song, MP ;

Mak, TCW ;

Wu, YJ .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (06) :1301-1306

[82] Palladium-Catalyzed Hiyama Cross-Coupling Reactions of Aryl Mesylates [J].

Zhang, Liang ;

Qing, Jiang ;

Yang, Pengyuan ;

Wu, Jie .

ORGANIC LETTERS, 2008, 10 (21) :4971-4974

[83] Palladium-catalyzed Hiyama cross-couplings of aryl arenesulfonates with arylsilanes [J].

Zhang, Liang ;

Wu, Jie .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (37) :12250-+

[84] Palladium-catalyzed suzuki-miyaura cross-couplings of aryl tosylates with potassium aryltrifluoroborates [J].

Zhang, Liang ;

Meng, Tianhao ;

Wu, Jie .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (24) :9346-9349

[85] General and efficient route for the synthesis of 3,4-disubstituted coumarins via Pd-catalyzed site-selective cross-coupling reactions [J].

Zhang, Liang ;

Meng, Tianhao ;

Fan, Renhua ;

Wu, He .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (19) :7279-7286

[86] Palladium-catalyzed Negishi cross-coupling reactions of unactivated alkyl iodides, bromides, chlorides, and tosylates [J].

Zhou, JR ;

Fu, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (41) :12527-12530

[87] NiCl2(PCy3)2:: A simple and efficient catalyst precursor for the Suzuki cross-coupling of aryl tosylates and arylboronic acids [J].

Zim, D ;

Lando, VR ;

Dupont, J ;

Monteiro, AL .

ORGANIC LETTERS, 2001, 3 (19) :3049-3051

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