Benzylation of nitroalkanes using copper-catalyzed thermal redox catalysis: toward the facile C-alkylation of nitroalkanes.

Benzylation of nitroalkanes using copper-catalyzed thermal redox catalysis: toward the facile C-alkylation of nitroalkanes.
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DOI:
10.1021/ja304561c
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发表时间:
2012-06-20
影响因子:
15
通讯作者:
Watson, Donald A.
Watson, Donald A.
中科院分区:
化学1区
文献类型:
--
作者:
Gildner, Peter G.;Gietter, Amber A. S.;Cui, Di;Watson, Donald A.

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一个多世纪以来,温和条件下硝基烷烃的C-烷基化一直是有机合成中的重大挑战。在此,我们报道了一种原位生成的简单 Cu(I) 催化剂,该催化剂对于使用丰富的苄基溴和相关杂芳族化合物进行硝基烷烃的 C-苄基化非常有效。我们认为该过程通过热氧化还原机制进行,可以在温和的反应条件下获得各种复杂的硝基烷烃,并且代表了开发用于硝基烷烃烷基化的通用催化系统的第一步。
The C-alkylation of nitroalkanes under mild conditions has been a significant challenge in organic synthesis for more than a century. Herein, we report a simple Cu(I) catalyst, generated in situ, that is highly effective for C-benzylation of nitroalkanes using abundant benzyl bromides and related heteroaromatic compounds. This process, which we believe proceeds via a thermal redox mechanism, allows access to a variety of complex nitroalkanes under mild reaction conditions and represents the first step towards developing a general catalytic system for the alkylation of nitroalkanes.
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