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Steric and electronic effects influencing β-aryl elimination in the Pd-catalyzed carbon-carbon single bond activation of triarylmethanols. | LitMetric

AI Article Synopsis

  • An analysis of palladium-catalyzed reactions has improved our understanding of how carbon-carbon single bonds in triarylmethanols can be broken down through a process called β-aryl elimination.
  • Experiments showed that aryl groups with ortho-substitutions are eliminated more easily than unsubstituted phenyl rings.
  • Additionally, the study found that substrates with strong electron-donating or withdrawing groups are more likely to undergo C-C bond cleavage compared to those with neutral substituents.

Article 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.

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Source
http://dx.doi.org/10.1021/jo302592gDOI Listing

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