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Iron-catalyzed borylation of alkyl electrophiles.

Authors :
Atack TC
Lecker RM
Cook SP
Source :
Journal of the American Chemical Society [J Am Chem Soc] 2014 Jul 09; Vol. 136 (27), pp. 9521-3. Date of Electronic Publication: 2014 Jun 23.
Publication Year :
2014

Abstract

The use of low-cost iron(III) acetoacetate (Fe(acac)3) and tetramethylethylenediamine (TMEDA) enables the direct cross-coupling of alkyl halides with bis(pinacolato)diboron. This approach allows for the borylation of activated or unactivated primary, secondary, and tertiary bromides. Moreover, even the borylation of benzylic or allylic chlorides, tosylates, and mesylates are possible. The reactions proceed under mild conditions at room temperature and show broad functional-group compatibility and "robustness" as measured by a modified Glorius robustness screen.

Details

Language :
English
ISSN :
1520-5126
Volume :
136
Issue :
27
Database :
MEDLINE
Journal :
Journal of the American Chemical Society
Publication Type :
Academic Journal
Accession number :
24955892
Full Text :
https://doi.org/10.1021/ja505199u