Palladium-catalyzed cross-alkynylation of aryl bromides by sodium tetraalkynylaluminates

被引:36
作者
Gelman, D
Tsvelikhovsky, D
Molander, GA
Blum, J [1 ]
机构
[1] Hebrew Univ Jerusalem, Dept Organ Chem, IL-91904 Jerusalem, Israel
[2] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA
关键词
D O I
10.1021/jo020169q
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Sodium tetraalkynylaluminates (1-4), prepared from NaAlH4 and terminal alkynes, cross-couple with aryl bromides in the presence of Pd(0) and Pd(II) catalysts. The reactions take place in boiling THF or DME. The process is applicable to both homo- and heterocyclic aryl bromides and can be used for conversion of polybromo compounds into polyalkynes. The reactions are high yielding and selective, free of undesired homocoupling and hydrogenolysis processes. The reagents selectively react with the ring-bound bromine atoms but do not affect chloro, cyano, triflate, or ester functions.
引用
收藏
页码:6287 / 6290
页数:4
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