Tetrahydrofuran ring opening and related reactions with an N-heterocyclic carbene-boryl trifluoromethanesulfonate

被引：17
|
作者：
Solovyev, Andrey [2 ]
Lacote, Emmanuel [1 ,3 ]
Curran, Dennis P. [2 ]
机构：
[1] Univ Lyon 1, Inst Chim Lyon, ESCPE Lyon, CNRS,UMR 5265, F-69616 Villeurbanne, France
[2] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
[3] UPMC Univ Paris 06, Inst Parisien Chim Mol, UMR CNRS 7201, F-75005 Paris, France
来源：
DALTON TRANSACTIONS | 2013年 / 42卷 / 03期
基金：
美国国家科学基金会;
关键词：
FRUSTRATED LEWIS PAIRS; CYCLIC ETHERS; BORANE; HYDROGEN; BORON; COMPLEXES; PHOTOPOLYMERIZATIONS; ACTIVATION; RADICALS;
D O I：
10.1039/c2dt31773g
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Reaction of the triflate group in dipp-Imd-BH2OTf with nucleophiles generally occurs by direct substitution to give products dipp-Imd-BH(2)Nu. In contrast, reaction of this boryl triflate with aryloxides (ArO-) in THF resulted in insertion of THF with ring opening in between the NHC-boryl electrophile and the aryloxide to give products dipp-Imd-BH2O(CH2)(4)OAr. The incorporation of THF was observed with other nucleophiles such as ethylthiolate and trimethylsilanolate whose conjugate acids have pK(a) values similar to that of phenol. The cleavage of ethyl acetate and oxetane is reported as well. A possible mechanism is proposed.
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页码：695 / 700
页数：6
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