Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 362, Issue 1, Pages 146-151Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201901203
Keywords
cross-coupling; Grignard reagents; Iron; homogeneous catalysis; propargylic bromides
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Funding
- Spanish MINECO [CTQ2016-79826-R]
- Spanish MINECO (Juan de la Cierva contract)
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An iron-catalysed Kumada-type cross-coupling reaction between aryl substituted propargylic bromides and arylmagnesium reagents has been developed. Propargylic coupling products were the main or only outcome, and propargyl/allene regioselectivity was shown to depend on the electronic nature of the substituents on the triple bond of the substrate and on the arylmagnesium halide. Best selectivities were observed when electron donating substituents were present in either reagent. The process is stereoespecific, occurs with configuration inversion and no carbon-based radicals seem to be involved in the mechanism.
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