Negishi Coupling of Secondary Alkylzinc Halides with Aryl Bromides and Chlorides

被引：199

作者：

Han, Chong ^{[1
]}

Buchwald, Stephen L. ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 22期

关键词：

CROSS-COUPLINGS; ORGANOZINC REAGENTS; ORGANIC HALIDES; CATALYST; DISCOVERY; GRIGNARD;

D O I：

10.1021/ja902046m

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient palladium-catalyzed process has been developed for Negishi coupling of secondary alkylzinc halides with a wide range of aryl bromides and activated aryl chlorides. A palladium catalyst composed of a new biaryidialkylphosphine ligand, CPhos, effectively promotes the rate of the reductive elimination step relative to the rate of the undesired B-hydride elimination. The broad substrate scope and excellent ratio of the desired secondary to the undesired primary coupling product make this method a powerful and reliable tool for C(sp(3))-C(sp(2)) bond formation.

引用

页码：7532 / +

页数：3

共 22 条

[1] Palladium catalyzed stereoselective cross-couplings and acylations of chiral secondary diorganozincs
Boudier, A
Knochel, P
[J]. TETRAHEDRON LETTERS, 1999, 40 (04) : 687 - 690
[2] Direct synthesis of 4-arylpiperidines via palladium/copper(I)-cocatalyzed Negishi coupling of a 4-piperidylzinc iodide with aromatic halides and triflates
Corley, EG
Conrad, K
Murry, JA
Savarin, C
Holko, J
Boice, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (15) : 5120 - 5123
[3] The first general method for palladium-catalyzed Negishi cross-coupling of aryl and vinyl chlorides:: Use of commercially available Pd(P(t-BU)3)2 as a catalyst
Dai, CY
Fu, GC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (12) : 2719 - 2724
[4] de Meijere A., 2004, METAL CATALYZED CROS
[5] Efficient cross-coupling of secondary alkyltrifluoroborates with aryl chlorides-reaction discovery using parallel microscale experimentation
Dreher, Spencer D.
Dormer, Peter G.
Sandrock, Deidre L.
Molander, Gary A.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) : 9257 - +
[6] Aryl-aryl bond formation one century after the discovery of the Ullmann reaction
Hassan, J
Sévignon, M
Gozzi, C
Schulz, E
Lemaire, M
[J]. CHEMICAL REVIEWS, 2002, 102 (05) : 1359 - 1469
[7] DICHLORO[1,1'-BIS(DIPHENYLPHOSPHINO)FERROCENE]PALLADIUM-(II) - AN EFFECTIVE CATALYST FOR CROSS-COUPLING OF SECONDARY AND PRIMARY ALKYL GRIGNARD AND ALKYLZINC REAGENTS WITH ORGANIC HALIDES
HAYASHI, T
KONISHI, M
KOBORI, Y
KUMADA, M
HIGUCHI, T
HIROTSU, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (01) : 158 - 163
[8] Palladium-tetraphosphine as catalyst precursor for high-turnover-number Negishi cross-coupling of alkyl- or phenylzinc derivatives with aryl bromides
Kondolff, Isabelle
Doucet, Henri
Santelli, Maurice
[J]. ORGANOMETALLICS, 2006, 25 (22) : 5219 - 5222
[9] Efficient synthesis of functionalized organozinc compounds by the direct insertion of zinc into organic iodides and bromides
Krasovskiy, Arkady
Malakhov, Vladimir
Gavryushin, Andrei
Knochel, Paul
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (36) : 6040 - 6044
[10] Superior effect of a π-acceptor ligand (Phosphine-Electron-Deficient olefin ligand) in the Negishi coupling involving alkylzinc reagents
Luo, Xiancai
Zhang, Heng
Duan, Hui
Liu, Oiang
Zhu, Wheng
Zhang, Tony
Lei, Aiwen
[J]. ORGANIC LETTERS, 2007, 9 (22) : 4571 - 4574

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