期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 83, 期 7, 页码 3806-3818出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b00151
关键词
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资金
- Swiss National Science Foundation [PYAPP2_160581]
- Swiss National Science Foundation (SNF) [PYAPP2_160581] Funding Source: Swiss National Science Foundation (SNF)
The formation of C-N bonds with aryl amines is one of the most widely studied reactions in organic chemistry. Despite this, it is still highly challenging, often requiring expensive, precious metal-based catalysts. Here we report an easy catalyst-free methodology for constructing C-N bonds. The method, which proceeds via the in situ formation of closed ring amidinium ions, allows the preparation of a series of symmetrical and/or unsymmetrical aryl diamines in notably high yields (82-98%) and purity and with a variety of different substituents. The methodology is shown successful for the preparation of aryl diamines having para- and/or meta-substituted carboxyl, nitro, bromo, methoxy, or methyl groups. This green synthetic pathway, which is catalyst free, requires only three steps, and proceeds without the need for purification. Further, it is a new sustainable, economically viable method to achieve an otherwise challenging bond formation.
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