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Beneficial Effects of Electrochemistry in Cross‐Coupling Reactions: Electroreductive Synthesis of 4‐Aryl‐ or 4‐Heteroaryl‐6‐pyrrolylpyrimidines
Author(s) -
Sengmany Stéphane,
Vasseur Stéphane,
Lajnef Abdelmoumen,
Le Gall Erwan,
Léonel Eric
Publication year - 2016
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.201600790
Subject(s) - chemistry , aryl , electrochemistry , halide , catalysis , coupling reaction , combinatorial chemistry , nickel , computational chemistry , coupling (piping) , organic chemistry , electrode , alkyl , mechanical engineering , engineering
The rarely described 4‐(hetero)aryl‐6‐pyrrolylpyrimidines are prepared by electroreductive nickel‐catalysed cross‐coupling reactions between aryl halides and chloropyrimidines. Inherent predictable issues of such metal‐catalysed reactions that involve or produce highly nitrogenated compounds – like catalyst poisoning – are tackled by the process described in this paper. The relevance of the strategy is validated by a thorough comparison of the results obtained under electrochemical conditions with those obtained under classical Suzuki–Miyaura conditions.