Here we report a metal-free iodine/tert-butyl hydroperoxide mediated reaction of N-substituted indoles with dimethylformamide (DMF) / dimethylacetamide (DMA). The reaction produces bis-and tris(indolyl)methanes (BIMs and TIMs), in which DMF/DMA provides the methylene (of BIMs) and methine carbons (of TIMs). We have established different optimized conditions for their synthesis. Iodine (10 mol %) with TBHP (in decane, 1.0 equivalent) in DMF/DMA at 130 8C is required for the BIMs synthesis, whereas iodine (20 mol %) with TBHP (in water, 3.0 equivalent) in DMF-H 2 O or DMA-H 2 O (9:1) is needed for the TIMs. This methodology could be used to synthesize a variety of BIMs and TIMs. We believe, this is the first report of their metal-free synthesis through CÀH functionalization using one carbon source. The use of inexpensive, metal-free and environmentally benign catalyst made the method handy.[a] Dr.

Divergent reactions of various 1-(aminoalkyl)naphthols and 2-(aminoalkyl)phenols (commonly known as Betti bases) with indoles under Brønsted acid catalysis is reported. With the reaction strategies, one can efficiently synthesize important indole derivatives such as 3-(α,α-diarylmethyl)indoles and chromeno [2,3-b]indoles. Furthermore, we disclose here a new C-C bond-cleavage reaction, in which naphthol and phenol behave as leaving groups to produce diarylmethanes.

No abstract

Synthesis of 1,3-oxazinesviacatalyst free C–H functionalization using molecular oxygen in water.

A copper-catalyzed benzoylation/formylation of naphthols and phenols via oxidative deamination of Betti bases.