Hybrid Lewis acid/hydrogen-bond donor receptor for fluoride

被引：90

作者：

Hudnall, Todd W. ^{[1
]}

Melaimi, Mohand ^{[1
]}

Gabbai, Francois P. ^{[1
]}

机构：

[1] Texas A&M Univ, Dept Chem, College Stn, TX 77843 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 13期

关键词：

D O I：

10.1021/ol060791v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

To verify if hydrogen-bond donor groups can assist fluoride binding at the boron center of triaryl boranes, o-(dimesitylboryl) trifluoroacetanilide has been synthesized. Reaction of this new borane with [n-Bu4N][F] in acetone affords the corresponding fluoroborate complex whose stability constant exceeds that of [Mes(3)BF](-) by at least 2 orders of magnitude. Presumably, the higher fluoride affinity of o-(dimesitylboryl)trifluoroacetanilide results from the cooperativity of the Lewis acidic boron center and the hydrogen-bond donor trifluoroacetamide group.

引用

页码：2747 / 2749

页数：3

共 26 条

[1] Beer PD, 2001, ANGEW CHEM INT EDIT, V40, P486, DOI 10.1002/1521-3773(20010202)40:3<486::AID-ANIE486>3.3.CO
[2] 2-G
[3] Selective electrochemical detection of hydrogen fluoride by ambiphilic ferrocene derivatives
Bresner, C
Aldridge, S
Fallis, IA
Jones, C
Ooi, LL
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (23) : 3606 - 3609
[4] BRIANCON D, 1997, REV RHUM, V64, P48
[5] Indole-based macrocycles as a class of receptors for anions
Chang, KJ
Moon, D
Lah, MS
Jeong, KS
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (48) : 7926 - 7929
[6] Bifunctional perfluoroaryl boranes: Synthesis and coordination chemistry with neutral Lewis base donors
Chase, PA
Henderson, LD
Piers, WE
Parvez, M
Clegg, W
Elsegood, MRJ
[J]. ORGANOMETALLICS, 2006, 25 (02) : 349 - 357
[7] New mononuclear and polynuclear perfluoroarylmetalate cocatalysts for stereospecific olefin polymerization
Chen, MC
Roberts, JAS
Marks, TJ
[J]. ORGANOMETALLICS, 2004, 23 (05) : 932 - 935
[8] On a quantitative scale for Lewis acidity and recent progress in polynitrogen chemistry
Christe, KO
Dixon, DA
McLemore, D
Wilson, WW
Sheehy, JA
Boatz, JA
[J]. JOURNAL OF FLUORINE CHEMISTRY, 2000, 101 (02) : 151 - 153
[9] Davis AP, 1999, ANGEW CHEM INT EDIT, V38, P2978
[10] Anion receptor chemistry: highlights from 1999
Gale, PA
[J]. COORDINATION CHEMISTRY REVIEWS, 2001, 213 : 79 - 128

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