Suzuki-Miyaura coupling reaction using pentafluorophenylboronic acid

被引：115

作者：

Korenaga, T ^{[1
]}

Kosaki, T ^{[1
]}

Fukumura, R ^{[1
]}

Ema, T ^{[1
]}

Sakai, T ^{[1
]}

机构：

[1] Okayama Univ, Grad Sch Nat Sci, Dept Synthet Chem, Okayama 7008530, Japan

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 22期

关键词：

D O I：

10.1021/ol051866i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] We have found new conditions for the Suzuki-Miyaura coupling reaction applicable to pentafluorophenylboronic acid (C6F5B(OH)2) (1), which is an inactive substrate under normal conditions. The reactions of 1 with phenyl iodide or bromide under Pd(PPh3)(4)/CsF/Ag2O or Pd-2(dba)(3)/P(t-Bu)(3)CsF/Ag2O catalytic system conditions gave 2,3,4,5,6-pentafluoro-1,1'-biphenyl (3a) in more than 90% yields. Combination of CsF and Ag2O was essential for promoting these reactions.

引用

页码：4915 / 4917

页数：3

共 37 条

[1] Deconstruction of Taft's σ* parameter:: QSAR meets QALE
Babij, C
Poë, AJ
[J]. JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2004, 17 (02) : 162 - 167
[2] Palladium catalysts for the Suzuki cross-coupling reaction: An overview of recent advances
Bellina, F
Carpita, A
Rossi, R
[J]. SYNTHESIS-STUTTGART, 2004, (15): : 2419 - 2440
[3] A novel Suzuki-type cross-coupling reaction of cyclopropylboronic esters with benzyl bromides
Chen, H
Deng, MZ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (10): : 1609 - 1613
[4] A novel stereocontrolled synthesis of 1,2-trans cyclopropyl ketones via Suzuki-type coupling of acid chlorides with cyclopropylboronic acids
Chen, H
Deng, MZ
[J]. ORGANIC LETTERS, 2000, 2 (12) : 1649 - 1651
[5] 2-(Fluorophenyl)pyridines by the Suzuki-Miyaura method:: Ag2O accelerates coupling over undesired ipso substitution (SNAr) of fluorine
Chen, J
Cammers-Goodwin, A
[J]. TETRAHEDRON LETTERS, 2003, 44 (07) : 1503 - 1506
[6] The trans influence of F, Cl, Br and I ligands in a series of square-planar Pd(II) complexes.: Relative affinities of halide anions for the metal centre in trans-[(Ph3P)2Pd(Ph)X]
Flemming, JP
Pilon, MC
Borbulevitch, OY
Antipin, MY
Grushin, VV
[J]. INORGANICA CHIMICA ACTA, 1998, 280 (1-2) : 87 - 98
[7] Molecular fluoro palladium complexes
Fraser, SL
Antipin, MY
Khroustalyov, VN
Grushin, VV
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (20) : 4769 - 4770
[8] Frisch M. J., 2016, J AM CHEM SOC, DOI DOI 10.1021/JA205566W
[9] Polyfluoroorganoboron oxygen compounds, part 3. The palladium-catalysed cross-coupling reaction of lithium polyfluorophenyltrimethoxyborates with 4-fluoroiodobenzene
Frohn, HJ
Adonin, NY
Bardin, VV
Starichenko, VF
[J]. JOURNAL OF FLUORINE CHEMISTRY, 2003, 122 (02) : 195 - 199
[10] Highly efficient cross-coupling reactions with the perfluoroorganotrifluoroborate salts K [RFBF3] (RF=C6F5, CF2=CF)
Frohn, HJ
Adonin, NY
Bardin, VV
Starichenko, VF
[J]. TETRAHEDRON LETTERS, 2002, 43 (45) : 8111 - 8114

← 1 2 3 4 →