Hydrodeboration of potassium polyfluoroaryl(fluoro)borates with alcohols

被引:9
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 [J].
Abo-Amer, A ;
Adonin, NY ;
Bardin, VV ;
Fritzen, P ;
Frohn, HJ ;
Steinberg, C .
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 [J].
Abo-Amer, Anwar ;
Frohn, Hermann-Josef ;
Steinberg, Christoph ;
Westphal, Ulrich .
JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (10) :1311-1323
[3]   Polyfluorinated organic compounds of boron [J].
Adonin, N. Yu ;
Bardin, V. V. .
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) [J].
Adonin, Nicolai Yu. ;
Bardin, Vadim V. ;
Frohn, Hermann-Josef .
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 [J].
Adonin, Nicolay Yu. ;
Babushkin, Dmitrii E. ;
Parmon, Valentin N. ;
Bardin, Vadim V. ;
Kostin, Gennadiy A. ;
Mashukov, Vasiliy I. ;
Frohn, Hermann-Josef .
TETRAHEDRON, 2008, 64 (25) :5920-5924
[7]   Polyfluoroorganoboron-oxygen compounds.: 4 [1] Lithium pentafluorophenyltrimethoxyborate, Li[C6F5B(OMe)3], reactions with selected electrophiles and nucleophiles [J].
Adonin, NY ;
Bardin, VV ;
Flörke, U ;
Frohn, HJ .
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