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Iron‐Catalyzed Cross‐Coupling of 1‐Alkynylcyclopropyl Tosylates and Related Substrates
Author(s) -
Tindall Daniel J.,
Krause Helga,
Fürstner Alois
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201600357
Subject(s) - chemistry , allene , electrophile , alkyl , catalysis , reagent , aryl , halide , ferric , reactivity (psychology) , coupling reaction , medicinal chemistry , organic chemistry , medicine , alternative medicine , pathology
1‐Alkynylcyclopropyl tosylates react with alkylmagnesium halides in the presence of catalytic ferric acetylacetonate [Fe(acac) 3 ] under net propargylic substitution; allene formation, which is the prevalent reactivity mode of propargylic substrates otherwise, was noticed as a side reaction only when branched alkyl‐ or aryl‐Grignard reagents were used. These transformations represent the first successful iron‐catalyzed cross‐coupling reactions of tert ‐alkyl electrophiles.