Divergent synthesis of bis(indolyl)methanes via FeIII-catalysed regioselective dehydrogenative coupling reactions: a biomimetic approach to 6,6′-bis-(debromo)-gelliusine F

The divergent dehydrogenative coupling reactions of tryptamines with the catalysis of nontoxic Fe-III salts in the presence of DDQ as the co-oxidant have been developed. Remarkably, the transformations feature a rapid and regioselective assembly of diverse 2,8 '- and N1,8 '-bis(indolyl) methane derivatives from readily-available starting materials by simply changing the Fe-III salt and reaction temperature. Besides, the fast reaction rate, mild reaction conditions, low catalyst cost and easy operations make this methodology quite useful. The synthetic utility was further demonstrated in the biomimetic synthesis of 6,6 '-bis-(debromo)-gelliusine F.

Automated summary

Divergent dehydrogenative coupling reactions of tryptamines with nontoxic Fe-III salts as catalysts and DDQ as the co-oxidant have been developed. This method enables rapid and regioselective assembly of diverse 2,8'- and N1,8'-bis(indolyl)methane derivatives from easily available starting materials by simply changing the Fe-III salt and reaction temperature. The fast reaction rate, mild reaction conditions, low catalyst cost, and ease of operation make this methodology highly useful. The synthetic utility of this method was further demonstrated in the biomimetic synthesis of 6,6'-bis-(debromo)-gelliusine F.