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Wagner, Andreas Johannes (2011): Oxidative Copper(I)-Mediated Cycloamination. Preparation and Reactions of Heteroaromatic Benzylic Zinc Compounds. Novel Preparation of Tertiary Benzylic and Phenethylic Amines. Dissertation, LMU München: Faculty of Chemistry and Pharmacy
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Abstract

1. It was demonstrated that the two-fold deprotonation of benzofuran-3-yl- and benzothiophen-3-ylanilines using nBuLi, followed by transmetalation using CuCl·2LiCl afforded cyclic amidocuprates which were readily oxidized using 2,3,5,6-tetrachlorobenzo-p-quinone (“chloranil”) to furnish new tetracyclic benzofuro- and benzothieno[2,3-b]indoles. 2. A method was developed, starting from heteroaryl organometallics, for the synthesis of non-conjugated heteroaromatic benzylic zinc compounds which could be reacted with a wide range of electrophiles. 3. The preparation of mixed aminals from Mannich’s cation and a range of metal amides was performed and their subsequent ionization to (methylene)iminium ions using trifluoroacetic anhydride was achieved. Trapping of these iminium ions with a range of organometallic substrates in a one-pot fashion led to the efficient formation of sterically hindered tertiary benzylic and phenethylic amines.