Hydrodeboration of potassium polyfluoroaryl(fluoro)borates with alcohols

被引:8
作者
Adonin, Nicolay Yu. [1 ,2 ]
Shabalin, Anton Yu. [1 ]
Bardin, Vadim V. [2 ,3 ]
机构
[1] SB RAS, GK Boreskov Inst Catalysis, Novosibirsk 630090, Russia
[2] Novosibirsk State Univ, Novosibirsk 630090, Russia
[3] SB RAS, NN Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia
关键词
Pentafluorophenyltrifluoroborate; Hydrodeboration; NMR spectroscopy; POLYFLUOROORGANOBORON-OXYGEN COMPOUNDS; CROSS-COUPLING REACTION; NUCLEAR-MAGNETIC-RESONANCE; BORONIC ACID; COMPLEXES; CATALYSTS; SALTS; (FLUOROORGANO)FLUOROBORANES; PENTAFLUOROPHENYLTRIFLUOROBORATE; FLUOROORGANO;
D O I
10.1016/j.jfluchem.2014.09.016
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Potassium polyfluoroaryltrifluoroborates, K[ArFBF3] (Ar-F = C6F5, HC6F4, MeC6F4, 4-MeOC6F4, 4-indol-1-ylC(6)F(4), 4-imidazol-1-ylC(6)F(4), 4-pyrazol-1-ylC(6)F(4), 2,4,6-C6F3H2 and 4-tetrafluoropyridyl), and K[(C6F6)(2)BF2] undergo hydrodeboration to ArFH in aliphatic alcohols at elevated temperature. At the same conditions, borates K[3,4,5-C6F3H2BF3], K[4-FC6H4BF3] and K[C6H5BF3] remain intact. The presence of base (Et3N, K2CO3 and NaOMe) retards or prevents conversion of K[C6F5BF3]. Attempted hydrodeboration of K[C6F5BF3] in MeCN failed. (C) 2014 Elsevier B.V. All rights reserved.
引用
收藏
页码:111 / 120
页数:10
相关论文
共 68 条
  • [1] Polyfluoroorganotrifluoroborates and -difluoroboranes: interesting materials in fluoroorgano and fluoroorgano-element chemistry
    Abo-Amer, A
    Adonin, NY
    Bardin, VV
    Fritzen, P
    Frohn, HJ
    Steinberg, C
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2004, 125 (11) : 1771 - 1778
  • [2] From hypervalent xenon difluoride and aryliodine(III) difluorides to onium salts: Scope and limitation of acidic fluoroorganic reagents in the synthesis of fluoroorgano xenon(II) and iodine(III) onium salts
    Abo-Amer, Anwar
    Frohn, Hermann-Josef
    Steinberg, Christoph
    Westphal, Ulrich
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (10) : 1311 - 1323
  • [3] Polyfluorinated organic compounds of boron
    Adonin, N. Yu
    Bardin, V. V.
    [J]. RUSSIAN CHEMICAL REVIEWS, 2010, 79 (09) : 757 - 785
  • [4] Adonin N. Yu., 2009, CHIM OGGI CHEM TODAY, V27, P31
  • [5] POLYFLUOROORGANOBORON-OXYGEN COMPOUNDS. 7+. STUDIES OF CONVERSION OF [(C6HnF5-n)B(OMe)3]- INTO [(C6HnF5-n)2B(OMe)2]- (n=0, 1)
    Adonin, Nicolai Yu.
    Bardin, Vadim V.
    Frohn, Hermann-Josef
    [J]. COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2008, 73 (12) : 1681 - 1692
  • [6] The effect of N-heterocyclic carbene ligands in the palladium-catalyzed cross-coupling reaction of K[C6F5BF3] with aryl iodides and aryl bromides
    Adonin, Nicolay Yu.
    Babushkin, Dmitrii E.
    Parmon, Valentin N.
    Bardin, Vadim V.
    Kostin, Gennadiy A.
    Mashukov, Vasiliy I.
    Frohn, Hermann-Josef
    [J]. TETRAHEDRON, 2008, 64 (25) : 5920 - 5924
  • [7] Polyfluoroorganoboron-oxygen compounds.: 4 [1] Lithium pentafluorophenyltrimethoxyborate, Li[C6F5B(OMe)3], reactions with selected electrophiles and nucleophiles
    Adonin, NY
    Bardin, VV
    Flörke, U
    Frohn, HJ
    [J]. ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 2005, 631 (13-14): : 2638 - 2646
  • [8] Bardin VV, 2002, Z ANORG ALLG CHEM, V628, P883, DOI 10.1002/1521-3749(200205)628:4<883::AID-ZAAC883>3.0.CO
  • [9] 2-A
  • [10] Bardin VV, 2002, MAIN GROUP MET CHEM, V25, P589