One-pot reduction of aryl iodides using 4-DMAP methiodide salt
One-pot reduction of aryl iodides using 4-DMAP methiodide salt
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DOI：
10.1055/s-2008-1078242
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发表时间：
2008-08-22
期刊：
影响因子：
2
通讯作者：
Turner, Andrew T.
中科院分区：
文献类型：
--
作者：
Garnier, Jean;Murphy, John A.;Turner, Andrew T.
一个有效的一锅程序，用于还原芳基碘到芳基阴离子使用结构简单的双吡啶叉电子供体，原位制备的4-DMAP甲基碘化物盐与碱处理。结果表明：（i）吡啶亚基卡宾可以很容易地用于分子间C-C键的形成，（ii）与基于双咪唑亚基的电子给体系统相比，双吡啶亚基表现出上级的稳健性，以及（iii）在简化的基于DMAP的给体中电子给体强度增强。氘代类似物的这种供体也提供了质子的来源时，芳基阴离子在原位淬灭的机械信息。
An efficient one-pot procedure is described for the reduction of aryl iodides to aryl anions using a structurally simple bis-pyridinylidene electron donor, prepared in situ by treating 4-DMAP methiodide salt with base. The results show (i) that pyridinylidene carbenes can be easily used for intermolecular C-C bond formation, (ii) that bis-pyridinylidenes demonstrate superior robustness compared to electron-donor systems based on bis-imidazolylidenes, and (iii) that electron-donor strength is enhanced in the simplified DMAP-based donor. Deuterated analogues of this donor also provide mechanistic information on the source of protons when the aryl anions are quenched in situ.