The direct use of ammonia in transition-metal promoted C−H bond amination for the synthesis of primary amines is considered to be one of the major challenges in synthetic organic chemistry. Herein, we report that such transformation can be successfully achieved via nickel-promoted amination of inert arene C−H bonds with ammonia gas assisted by an 8-amino-quinoline directing group.

A highly monoselective synthesis of ferrocenyl alkynes was achieved via Cu-promoted ferrocene C­(sp2)–H bond activations. The reaction employs an 8-aminoquinoline group as the directing group and terminal alkynes as the alkyne source. It was found the alkynylation products actually complex with the in situ generated Cu­(I) ions to give robust and stable alkyne π-copper complexes. In addition, these alkyne π-copper complexes could be freed of the copper ions to give various ferrocenyl alkynes in almost quantitative yields. The test results also showed that the alkyne π-copper complexes could be reformed from the free alkynes upon treating them with Cu­(I) salts.

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A novel and efficient method for highly regioselective cyanomethylation of 8-aminoquinoline amides at C5 position was developed. Such reactions proceed under transition metalfree and base-free conditions. This protocol features simple operation, high efficiency, good functional group tolerance and broad substrate scope. Moreover, the etherification or acetonation products were also obtained when acetonitrile was replaced by ethers or acetone, and a radical process was involved in the reaction.

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