Photostimulated reactions of phenylacetic acid dianions with aryl halides.Influence of the metallic cation on the regiochemistry of arylation

Authors
Nwokogu, GC Wong, JW Greenwood, TD Wolfe, JF
Citation
Gc. Nwokogu et al., Photostimulated reactions of phenylacetic acid dianions with aryl halides.Influence of the metallic cation on the regiochemistry of arylation, ORG LETT, 2(17), 2000, pp. 2643-2646
Citations number
21
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
17
Year of publication
2000
Pages
2643 - 2646
Database
ISI
SICI code
1523-7060(20000824)2:17<2643:PROPAD>2.0.ZU;2-2
Abstract
[GRAPHICS] Phenylacetic acid dianions react via what appears to be an S(RN)1 process w ith aryl halides under photostimulation to afford aryl substitution product s 5 and 6. When the counterion is K+, only 4-biphenylacetic acids 5 are obt ained, Both alpha- and para-coupling occurs with Na+ to give a mixture of 5 end 6, while exclusive formation of diphenylacetic acids 6 is observed wit h the dilithio salt of 1.