Efficient catalyst for the Suzuki-Miyaura coupling of potassium aryl trifluoroborates with aryl chlorides

被引：149

作者：

Barder, TE ^{[1
]}

Buchwald, SL ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 16期

关键词：

D O I：

10.1021/ol0491686

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of aryl- and heteroaryl chlorides with potassium aryl- and heteroaryltrifluoroborates have been accomplished with the supporting ligand S-Phos in good to excellent yield. Hindered biaryls and substrates containing a variety of functional groups can be prepared. Suzuki-Miyaura couplings of a 3-pyridyl boron-based nucleophile with aryl- and heteroaryl chlorides proceed in good to very good yield.

引用

页码：2649 / 2652

页数：4

共 17 条

[1] Synthesis and cross-coupling reactions of tetra alkylammonium organotrifluoroborate salts
Batey, RA
Quach, TD
[J]. TETRAHEDRON LETTERS, 2001, 42 (52) : 9099 - 9103
[2] Bonnet V, 2002, SYNLETT, P1008
[3] Iron-catalyzed cross-coupling reactions
Fürstner, A
Leitner, A
Méndez, M
Krause, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (46) : 13856 - 13863
[4] 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
[5] ISHIKURA M, 1985, HETEROCYCLES, V23, P2375
[6] Recent applications of the Suzuki-Miyaura cross-coupling reaction in organic synthesis
Kotha, S
Lahiri, K
Kashinath, D
[J]. TETRAHEDRON, 2002, 58 (48) : 9633 - 9695
[7] Advances in the Negishi coupling
Lessene, G
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 2004, 57 (01) : 107 - 107
[8] Versatile catalysts for the Suzuki cross-coupling of arylboronic acids with aryl and vinyl halides and triflates under mild conditions
Littke, AF
Dai, CY
Fu, GC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) : 4020 - 4028
[9] Miyaura N, 2002, TOP CURR CHEM, V219, P11
[10] Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of potassium aryl- and heteroaryltrifluoroborates
Molander, GA
Biolatto, B
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) : 4302 - 4314

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