An efficient process for pd-catalyzed C-N cross-coupling reactions of aryl iodides: insight into controlling factors.

An efficient process for pd-catalyzed C-N cross-coupling reactions of aryl iodides: insight into controlling factors.
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DOI:
10.1021/ja901414u
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发表时间:
2009-04-29
影响因子:
15
通讯作者:
Buchwald SL
Buchwald SL
中科院分区:
化学1区
文献类型:
--
作者:
Fors BP;Davis NR;Buchwald SL

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研究了钯催化的碘代芳烃的C-N交叉偶联反应。NaI被证明对这些过程有显着的抑制作用。通过切换到碘化物副产物不溶于其中的溶剂系统,芳基碘化物的反应以与芳基氯化物和溴化物相同的效率完成。使用基于某些联芳基膦配体的催化剂体系,芳基碘以高产率成功地与一系列伯胺和仲胺反应。最后,杂芳基胺和杂芳基碘的反应也以高产率进行。
An investigation into Pd-catalyzed C–N cross-coupling reactions of aryl iodides is described. NaI is shown to have a significant inhibitory effect on these processes. By switching to a solvent system in which the iodide byproduct was insoluble, reactions of aryl iodides were accomplished with the same efficiencies as aryl chlorides and bromides. Using catalyst systems based on certain biarylphosphine ligands, aryl iodides were successfully reacted with an array of primary and secondary amines in high yields. Lastly, reactions of heteroarylamines and heteroaryliodides were also conducted in high yields.
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