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Catalytic C‐Alkylation of Pyrroles with Primary Alcohols: Hans Fischer's Alkali and a New Method with Iridium P,N,P‐Pincer Complexes
Author(s) -
Koller Sebastian,
Blazejak Max,
Hintermann Lukas
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800146
Subject(s) - alkylation , chemistry , iridium , catalysis , pincer movement , homogeneous catalysis , alkali metal , transition metal , homogeneous , medicinal chemistry , base (topology) , organic chemistry , primary (astronomy) , mathematical analysis , physics , mathematics , thermodynamics , astronomy
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 were found to take place under basic alcoholic conditions (Hans Fischer alkylation) in the absence of transition‐metal catalysts; by means of a heterogeneous Pd/C catalyst in the presence of base; and finally by means of homogeneous transition‐metal catalysis combining a base and iridium pincer complexes generated in situ that have not previously been used in HAT alkylations of heterocycles.