Activation of Alkyl C-F Bonds by B(C6F5)3: Stoichiometric and Catalytic Transformations

被引:129
作者
Caputo, Christopher B. [1 ]
Stephan, Douglas W. [1 ]
机构
[1] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
FRUSTRATED LEWIS PAIRS; OXIDATIVE ADDITION; C(SP(3))-F BONDS; REACTIVITY; MECHANISM; HYDRODEFLUORINATION; DIHYDROGEN; CLEAVAGE; ACID; ION;
D O I
10.1021/om200885c
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The Lewis acid B(C6F5)(3) is shown to activate a series of alkyl fluorides. In stoichiometric reactions, treatment of sterically demanding phosphines with B(C6F3)(3)/alkyl fluorides gives phosphonium fluoroborate salts while treatment of B(C6F5)(3)/alkyl fluorides with the salts [tBu(3)PX][CB(C6F5)(3)] (X = H, PhS) gives the alkane and the salt byproduct [tBu(3)PX][FB(C6F5)(3)]. These fluoroalkanes are also catalytically converted to the corresponding alkanes by reaction of the fluoroalkane and Et3SiH using B(C6F5)(3) as the catalyst.
引用
收藏
页码:27 / 30
页数:4
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