Fe-catalyzed reductive couplings of terminal (hetero)aryl alkenes and alkyl halides under aqueous micellar conditions.

Fe-catalyzed reductive couplings of terminal (hetero)aryl alkenes and alkyl halides under aqueous micellar conditions.
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在水性胶束条件下,Fe 催化末端(杂)芳基烯烃和卤代烷的还原偶联。

DOI:
10.1021/jacs.9b04510
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发表时间:
2019
影响因子:
15
通讯作者:
B. Lipshutz
B. Lipshutz
中科院分区:
化学1区
文献类型:
--
作者:
Haobo Pang;Ye Wang;F. Gallou;B. Lipshutz

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乙烯基取代的芳族或杂芳族与烷基溴或烷基碘的组合在Zn和催化量的Fe(II)盐存在下导致净还原偶联。新的 C-C 键在室温下在 al-kene 的  位点区域特异性形成。偶联仅发生在水性胶束介质中,其中可能发生非典型碳负离子(与自由基相反)过程,并得到了几个对照实验的支持。提出了一种基于这些数据的机制。
The combination of a vinyl-substituted aromatic or heteroaromatic and an alkyl bromide or iodide leads, in the presence of Zn and a catalytic amount of an Fe(II) salt, to a net reductive coupling. The new C-C bond is regiospecifically formed at rt at the -site of the al-kene. The coupling only occurs in an aqueous micellar medium, where an atypical carbanionic, as opposed to radical, process is likely, supported by several control experiments. A mechanism based on these data is proposed.
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