European Journal of Organic Chemistry
European Journal of Organic Chemistry
5 years ago

Catalytic C-Alkylation of Pyrroles with Primary Alcohols: Hans Fischer's Alkali, and a New Spin with Iridium P,N,P-Pincer Complexes

Sebastian Koller, Lukas Hintermann, Max Blazejak
Hydrogen autotransfer alkylation (HAT or "borrowing hydrogen" alkylation) of heteroaromatic compounds has been studied with a range of substrates recently, but pyrroles have been largely absent from such studies. The conditions for HAT-alkylations of pyrroles were investigated under a variety of conditions and found to take place a) under basic alcoholic conditions (Hans-Fischer- alkylation) in the absence of transition metal catalysts; b) by means of a heterogeneous Pd/C catalyst in the presence of base; c) and finally by means of homogeneous transition metal catalysis combining base and in situ generated iridium pincer complexes introduced by Kempe and not previously used in HAT-alkylations of heterocycles.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/ejoc.201800146

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