One-pot synthesis of symmetrical and unsymmetrical bisarylethynes by a modification of the Sonogashira coupling reaction

被引：279

作者：

Mio, MJ

Kopel, LC

Braun, JB

Gadzikwa, TL

Hull, KL

Brisbois, RG

Markworth, CJ

Grieco, PA

机构：

[1] Macalester Coll, Dept Chem, St Paul, MN 55105 USA

[2] Montana State Univ, Dept Chem & Biochem, Bozeman, MT 59717 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 19期

关键词：

D O I：

10.1021/ol026266n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A modification of the Sonogoshira coupling reaction employing an amidine base and a substoichiometric amount of water generates symmetrical and unsymmetrical bisarylethynylenes in one pot through in situ deprotection of trimethylsilylethynylene-added intermediates.

引用

页码：3199 / 3202

页数：4

共 29 条

[21] PHASE-TRANSFER PD(O) CATALYZED POLYMERIZATION REACTIONS .1. SYNTHESIS OF 1,2-(4,4'-DIALKOXYARYL)ACETYLENE MONOMERS AND 1,4-BIS[2-(4',4''-DIALKOXYPHENYL)ETHYNYL]BENZENE DERIVATIVES BY PHASE-TRANSFER PD(O)/CU(I) CATALYZED COUPLING REACTIONS
PUGH, C
PERCEC, V
[J]. JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 1990, 28 (05) : 1101 - 1126
[22] Optically active BINOL core-based phenyleneethynylene dendrimers for the enantioselective fluorescent recognition of amino alcohols
Pugh, VJ
Hu, QS
Zuo, XB
Lewis, FD
Pu, L
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (18) : 6136 - 6140
[23] A modified procedure for sonogashira couplings:: Synthesis and characterization of a bisporphyrin, 1,1-bis[zinc(II) 5′-ethynyl-10′,15′,20′-trimesitylporphyrinyl] methylenecyclohexane
Shultz, DA
Gwaltney, KP
Lee, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (12) : 4034 - 4038
[24] Sonogashira K, 1998, METAL-CATALYZED CROSS-COUPLING REACTIONS, P203
[25] CONVENIENT SYNTHESIS OF ACETYLENES - CATALYTIC SUBSTITUTIONS OF ACETYLENIC HYDROGEN WITH BROMOALKENES, IODOARENES, AND BROMOPYRIDINES
SONOGASHIRA, K
TOHDA, Y
HAGIHARA, N
[J]. TETRAHEDRON LETTERS, 1975, (50) : 4467 - 4470
[26] Stang P. J., 1995, MODERN ACETYLENE CHE
[27] Molecular electronics. Synthesis and testing of components
Tour, JM
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (11) : 791 - 804
[28] Carbon networks based on dehydrobenzoannulenes. 4. Synthesis of "star" and "trefoil" graphdiyne substructures via sixfold cross-coupling of hexaiodobenzene
Wan, WB
Haley, MM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (11) : 3893 - 3901
[29] Efficient Sonogashira, reactions of aryl bromides with alkynylsilanes catalyzed by a palladium/imidazolium salt system
Yang, CL
Nolan, SP
[J]. ORGANOMETALLICS, 2002, 21 (06) : 1020 - 1022

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