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

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