Title

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

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