Nickel-catalysed hydroarylation of alkynes using arylboron compounds: selective synthesis of multisubstituted arylalkenes and aryldienes

被引：95

作者：

Shirakawa, E ^{[1
]}

Takahashi, G ^{[1
]}

Tsuchimoto, T ^{[1
]}

Kawakami, Y ^{[1
]}

机构：

[1] Japan Adv Inst Sci & Technol, Grad Sch Med Sci, Tatsunokuchi, Ishikawa 9231292, Japan

来源：

CHEMICAL COMMUNICATIONS | 2001年 / 24期

关键词：

D O I：

10.1039/b107866f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Bis(1,5-cyclooctadiene)nickel was found to be an effective catalyst for the addition of the aryl group of arylboron compounds to alkynes in the presence of a proton source, which gives various multisubstituted alkenylarenes or dienylarenes selectively.

引用

页码：2688 / 2689

页数：2

共 15 条

[1]

Brase S, 1998, METAL-CATALYZED CROSS-COUPLING REACTIONS, P99

[2] FINE FEATHERS MAKE FINE BIRDS - THE HECK REACTION IN MODERN GARB [J].

DE MEIJERE, A ;

MEYER, FE .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1994, 33 (23-24) :2379-2411

[3] REACTIVITY OF ORGANOMAGNESIUM WITH ACETYLENIC-COMPOUNDS IN PRESENCE OF NICKEL-COMPLEX (PPH3)2NICL2 [J].

DUBOUDIN, JG ;

JOUSSEAUME, B ;

SAUX, A .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1978, 162 (02) :209-222

[4]

Heck R.F., 1991, Comprehensive Organic Synthesis, V4, P833, DOI DOI 10.1016/B978-0-08-052349-1.00110-4

[5] Highly efficient Pd-catalyzed coupling of arenes with olefins in the presence of tert-butyl hydroperoxide as oxidant [J].

Jia, CG ;

Lu, WJ ;

Kitamura, T ;

Fujiwara, Y .

ORGANIC LETTERS, 1999, 1 (13) :2097-2100

[6] Efficient activation of aromatic C-H bonds for addition to C-C multiple bonds [J].

Jia, CG ;

Piao, DG ;

Oyamada, JZ ;

Lu, WJ ;

Kitamura, T ;

Fujiwara, Y .

SCIENCE, 2000, 287 (5460) :1992-1995

[7] Novel Pd(II)- and Pt(II)-catalyzed regio- and stereoselective trans-hydroarylation of alkynes by simple arenes [J].

Jia, CG ;

Lu, WJ ;

Oyamada, J ;

Kitamura, T ;

Matsuda, K ;

Irie, M ;

Fujiwara, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (30) :7252-7263

[8] ELECTROPHILIC ALKENYLATION OF AROMATICS WITH PHENYLACETYLENE OVER ZEOLITE HSZ-360 [J].

SARTORI, G ;

BIGI, F ;

PASTORIO, A ;

PORTA, C ;

ARIENTI, A ;

MAGGI, R ;

MORETTI, N ;

GNAPPI, G .

TETRAHEDRON LETTERS, 1995, 36 (50) :9177-9180

[9] Nickel-catalyzed acylstannylation of 1,3-dienes:: Synthesis and reaction of ε-oxoallylstannanes [J].

Shirakawa, E ;

Nakao, Y ;

Yoshida, H ;

Hiyama, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (37) :9030-9031

[10] Nickel-catalyzed carbostannylation of alkynes with allyl-, acyl-, and alkynylstannanes: Stereoselective synthesis of trisubstituted vinylstannanes [J].

Shirakawa, E ;

Yamasaki, K ;

Yoshida, H ;

Hiyama, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (43) :10221-10222

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