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Evidence for in situ catalyst modification during the Pd-catalyzed conversion of aryl triflates to aryl fluorides.

Authors :
Maimone TJ
Milner PJ
Kinzel T
Zhang Y
Takase MK
Buchwald SL
Source :
Journal of the American Chemical Society [J Am Chem Soc] 2011 Nov 16; Vol. 133 (45), pp. 18106-9. Date of Electronic Publication: 2011 Oct 21.
Publication Year :
2011

Abstract

A mechanistic investigation of the Pd-catalyzed conversion of aryl triflates to fluorides is presented. Studies reveal that C-F reductive elimination from a LPd(II)(aryl)F complex (L = t-BuBrettPhos or RockPhos) does not occur when the aryl group is electron rich. Evidence is presented that a modified phosphine, generated in situ, serves as the actual supporting ligand during catalysis with such substrates. A preliminary study of the reactivity of a LPd(II)(aryl)F complex based on this modified ligand is reported.

Details

Language :
English
ISSN :
1520-5126
Volume :
133
Issue :
45
Database :
MEDLINE
Journal :
Journal of the American Chemical Society
Publication Type :
Academic Journal
Accession number :
21999801
Full Text :
https://doi.org/10.1021/ja208461k