A very simple synthesis of chloroalkenes and chlorodienes by selective Suzuki couplings of 1,1-and 1,2-dichloroethylene

被引：30

作者：

Barluenga, J ^{[1
]}

Moriel, P ^{[1
]}

Aznar, F ^{[1
]}

Valdés, C ^{[1
]}

机构：

[1] Univ Oviedo, Inst Quim Organomet Enrique Moles, E-33006 Oviedo, Spain

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2006年 / 348卷 / 03期

关键词：

boronic acids; chloroalkenes; cross-coupling; palladium; Suzuki reaction;

D O I：

10.1002/adsc.200505302

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Chloroalkenes, important building blocks for cross-coupling reactions, are prepared in one step by the Suzuki reaction of 1,1-dichloroethylene and 1,2-dichloroethylene with alkenyl- and arylboronic acids. Under the proper reaction conditions, it is possible to obtain the monocoupling reaction to provide the corresponding chloroalkenes with good yields. This method represents an excellent route for the preparation of chloroalkenes and chlorodienes from commercially available starting materials.

引用

页码：347 / 353

页数：7

共 41 条

[1] Alami M, 2000, SYNTHESIS-STUTTGART, P1499
[2] A convenient synthesis of (Z)-1-chloro-1-alkenes and (Z)-1-chloro-2-alkoxy-1-alkenes
Baati, R
Barma, DK
Krishna, UM
Mioskowski, C
Falck, JR
[J]. TETRAHEDRON LETTERS, 2002, 43 (06) : 959 - 961
[3] BARDER TE, 2001, J AM CHEM SOC, V42, P4087
[4] Palladium-catalyzed amination of 1-bromo- and 1-chloro-1,3-butadienes:: A general method for the synthesis of 1-amino-1,3-butadienes
Barluenga, J
Aznar, F
Moriel, P
Valdés, C
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) : 1697 - 1701
[5] Palladium catalyzed amination of vinyl chlorides:: a new entry to imines, enamines and 2-amino-1,3-butadienes
Barluenga, J
Fernández, MA
Aznar, F
Valdés, C
[J]. CHEMICAL COMMUNICATIONS, 2004, (12) : 1400 - 1401
[6] Palladium-catalyzed cross-coupling reactions of amines with alkenyl bromides:: A new method for the synthesis of enamines and imines
Barluenga, J
Fernández, MA
Aznar, F
Valdés, C
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (02) : 494 - 507
[7] Novel method for the synthesis of enamines by palladium catalyzed amination of alkenyl bromides
Barluenga, J
Fernández, MA
Aznar, F
Valdés, C
[J]. CHEMICAL COMMUNICATIONS, 2002, (20) : 2362 - 2363
[8] Barluenga J, 1999, ALDRICHIM ACTA, V32, P4
[9] PYROLYTIC GENERATION AND THERMAL REARRANGEMENT OF A 2-SILAINDENE
BARTON, TJ
BURNS, GT
[J]. ORGANOMETALLICS, 1982, 1 (11) : 1455 - 1458
[10] HYDROBORATION .39. 1,3,2-BENZODIOXABOROLE (CATECHOLBORANE) AS A NEW HYDROBORATION REAGENT FOR ALKENES AND ALKYNES - GENERAL SYNTHESIS OF ALKANEBORONIC AND ALKENEBORONIC ACIDS AND ESTERS VIA HYDROBORATION - DIRECTIVE EFFECTS IN HYDROBORATION OF ALKENES AND ALKYNES WITH CATECHOLBORANE
BROWN, HC
GUPTA, SK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (18) : 5249 - 5255

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