Reversible C-F bond formation and the Au-catalyzed hydrofluorination of alkynes

被引：292
作者：
Akana, Jennifer A. [1 ]
Bhattacharyya, Koyel X. [1 ]
Mueller, Peter [1 ]
Sadighi, Joseph P. [1 ]
机构：
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 25期
关键词：
D O I：
10.1021/ja0723784
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The gold(I) fluoride complex [(SIPr)AuF] [SIPr = 1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene] reacts reversibly with 3-hexyne to form a (beta-fluorovinyl)gold(I) species. The more stable fluorovinyl complex trans-{(SIPr)Au[(Ph)CC(F)CH3]}, formed by addition of [(SIPr)AuF] across 1-phenyl-1-propyne, has been characterized crystallographically. Both the protonolysis of a (fluorovinyl)gold complex and the reaction of a cationic (alkyne)gold(I) complex with the mild HF source Et3N center dot 3HF result in fluoroalkene formation. Electrophilic gold(I) complexes, supported by N-heterocyclic carbene ligands and generated in situ, catalyze the trans-hydrofluorination of internal alkynes at room temperature. This catalysis represents a new, selective, and potentially versatile method for the synthesis of fluoroalkenes.
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页码：7736 / +
页数：3
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