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钯催化芳基碘化物与甲锡烷基胂和甲锡烷基锑的一锅法交叉偶联反应。

One-pot palladium-catalyzed cross-coupling reaction of aryl iodides with stannylarsanes and stannylstibanes.

作者信息

Bonaterra Mariana, Martín Sandra E, Rossi Roberto A

机构信息

INFIQC, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Córdoba, 5000, Argentina.

出版信息

Org Lett. 2003 Jul 24;5(15):2731-4. doi: 10.1021/ol0349357.

Abstract

[reaction: see text] The reaction of Ph(3)As and Ph(3)Sb with Na metal in liquid ammonia gives Ph(2)M(-) ions (M = As, Sb) that react with n-Bu(3)SnCl to afford n-Bu(3)Sn-MPh(2) (1). The ammonia was allowed to evaporate, and toluene was added. The Pd-catalyzed cross-coupling reactions of these stannanes with aryl iodides afford functionalized triaryl-arsanes and triaryl-stibanes in high yields in a one-pot procedure (80-99%). The use of the commercially available, air-stable, and inexpensive Ph(3)M as the initial reagent and the one-pot process make this method a useful approach. This is the first report on the synthesis of 1 and the exploration of its chemistry.

摘要

[反应:见正文] 三苯基砷(Ph(3)As)和三苯基锑(Ph(3)Sb)与金属钠在液氨中反应生成Ph(2)M⁻离子(M = As,Sb),该离子与正丁基三苯基锡(n-Bu(3)SnCl)反应得到正丁基三苯基锡-二苯基M(1)。使氨蒸发,然后加入甲苯。这些锡烷与芳基碘化物的钯催化交叉偶联反应在一锅法中以高产率(80 - 99%)得到官能化的三芳基砷烷和三芳基锑烷。使用市售的、空气稳定且廉价的Ph(3)M作为起始试剂以及一锅法使得该方法成为一种有用的方法。这是关于1的合成及其化学性质探索的首次报道。

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