- Catalyst-Free Synthesis of Aryl Diamines via a Three-Step Reaction Process
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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.
- Bulut, Safak,Queen, Wendy L.
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p. 3806 - 3818
(2018/04/14)
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- A convenient one-pot synthesis of symmetric secondary and tertiary vicinal diamines
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A convenient one-pot synthesis of symmetric vicinal diamines utilizing sodium borohydride/trifluoroacetic acid reduction methodology is described.
- Nutaitis
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p. 1081 - 1085
(2007/10/02)
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- A Novel Method for the Synthesis of Symmetrical Vicinal Tertiary and Secondary Diamines
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A variety of symmetrical vicinal tertiary and secondary diamines are readily prepared in good to excellent yields by either Grignard reaction or reduction of the glyoxal bisproducts with benzotriazole and secondary or primary amines.
- Katritzky, Alan R.,Fan, Wei-Qiang,Fu, Cong
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p. 3209 - 3213
(2007/10/02)
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