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Iron‐Catalyzed Coupling of Aryl Grignard Reagents with Alkyl Halides: A Competitive Hammett Study
Author(s) -
Hedström Anna,
Bollmann Ulla,
Bravidor Jenny,
Norrby PerOla
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201100467
Subject(s) - transmetalation , aryl , electrophile , chemistry , catalysis , reagent , alkyl , nucleophile , selectivity , halide , coupling (piping) , oxidative coupling of methane , oxidative addition , grignard reagent , medicinal chemistry , organic chemistry , combinatorial chemistry , materials science , metallurgy
Competing for electrophiles : The elusive iron‐catalyzed CC coupling reaction was investigated and analyzed by a Hammett study of the nucleophilic partner. This required finding conditions in which the iron catalyst is stable in the presence of an excess of the Grignard reagent. The selectivity‐determining step seems to be the transmetalation, occurring either before or after the oxidative addition step (see scheme).