Steric and Electronic Effects Influencing β-Aryl Elimination in the Pd-catalyzed Carbon-Carbon Single Bond Activation of Triarylmethanols
Document Type
Article
Publication Date
1-24-2013
Publication Source
Journal of Organic Chemistry
Volume Number
78
Issue Number
4
First Page
1665
Last Page
1669
Publisher
American Chemical Society
ISSN
0022-3263
Abstract
An analysis of the palladium-catalyzed activation of carbon–carbon single bonds within triarylmethanols has led to a greater understanding of factors influencing the β-aryl elimination process responsible for C–C bond cleavage. A series of competition reactions were utilized to determine that β-aryl elimination of aryl substituents containing ortho-substitution proceeds with significant preference to unsubstituted phenyl rings. Further experiments indicate that substrates containing either strongly donating or withdrawing substituents are cleaved from triarylmethanols more readily than relatively neutral species.
Keywords
C-C-BOND; H BOND; ALPHA, ALPHA-DISUBSTITUTED ARYLMETHANOLS; OXIDATIVE ADDITION; IMINYL COMPLEXES; CLEAVAGE; RHODIUM; NICKEL; BENZONITRILE; REACTIVITY
Recommended Citation
Bour, James R., Jacob C. Green, Valerie J. Winton and Jeffrey B. Johnson. "Steric and Electronic Effects Influencing Β-Aryl Elimination in the Pd-Catalyzed Carbon-Carbon Single Bond Activation of Triarylmethanols." Journal of Organic Chemistry 78, no. 4 (2013). http://pubs.acs.org/doi/abs/10.1021/jo302592g
