Copper-catalyzed cross-coupling reaction of Grignard reagents with primary-alkyl halides: Remarkable effect of 1-phenylpropyne

被引：172

作者：

Terao, Jun

Todo, Hirohisa

Begum, Shameem Ara

Kuniyasu, Hitoshi

Kambe, Nobuaki

机构：

[1] Osaka Univ, Grad Sch Engn, Dept Appl Chem & Sci, Suita, Osaka 5650871, Japan

[2] Osaka Univ, Grad Sch Engn, Technol Ctr Atoms Mol & Ions Control, Suita, Osaka 5650871, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 12期

关键词：

alkynes; copper; cross-coupling; Grignard reagents;

D O I：

10.1002/anie.200603451

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) A general get-together: The Cu-catalyzed cross-coupling reaction of primary-alkyl halides with primary-, secondary-, and tertiary-alkyl and phenyl Grignard reagents proceeds efficiently in THF under reflux in the presence of 1-phenylpropyne (see scheme). The reaction is also applicable to alkyl mesylates (OMs) and tosylates (OTs). The reactivities of alkyl-X with a Grignard reagent increase in the order X = Cl < F < OMs < OTs < Br. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：2086 / 2089

页数：4

共 42 条

[1] EVIDENCE FOR A SINGLE ELECTRON-TRANSFER MECHANISM IN REACTIONS OF LITHIUM DIORGANOCUPRATES WITH ORGANIC HALIDES
ASHBY, EC
DEPRIEST, RN
TUNCAY, A
SRIVASTAVA, S
[J]. TETRAHEDRON LETTERS, 1982, 23 (50) : 5251 - 5254
[2] EVIDENCE FOR SINGLE ELECTRON-TRANSFER IN THE REACTIONS OF LITHIUM DIMETHYLCUPRATE WITH ALKYL-HALIDES
ASHBY, EC
COLEMAN, D
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (20) : 4554 - 4565
[3] REACTIONS OF NEW ORGANOCUPRATES .2. SUBSTITUTION-REACTIONS OF ALKYL, CYCLOALKYL, AND ARYL HALIDES WITH LICU2(CH3)3, LI2CU(CH3)3, AND LI2CU3(CH3)5
ASHBY, EC
LIN, JJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (17) : 2805 - 2808
[4] Scope and utility of a new soluble copper catalyst [CuBr-LiSPh-LiBr-THF]: A comparison with other copper catalysts in their ability to couple one equivalent of a grignard reagent with an alkyl sulfonate
Burns, DH
Miller, JD
Chan, HK
Delaney, MO
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (09) : 2125 - 2133
[5] Cu-catalyzed alkylation of Grignard reagents:: A new efficient procedure
Cahiez, G
Chaboche, C
Jézéquel, M
[J]. TETRAHEDRON, 2000, 56 (18) : 2733 - 2737
[6] Cardenas D. J., 1999, ANGEW CHEM, V111, P3201
[7] Advances in functional-group-tolerant metal-catalyzed alkyl-alkyl cross-coupling reactions
Cárdenas, DJ
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (04) : 384 - 387
[8] Cárdenas DJ, 1999, ANGEW CHEM INT EDIT, V38, P3018, DOI 10.1002/(SICI)1521-3773(19991018)38:20<3018::AID-ANIE3018>3.0.CO
[9] 2-F
[10] CARDENAS DJ, 2003, ANGEW CHEM, V115, P557

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