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Palladium-catalyzed ortho-selective C-H deuteration of arenes: evidence for superior reactivity of weakly coordinated palladacycles. | LitMetric

Palladium-catalyzed ortho-selective C-H deuteration of arenes: evidence for superior reactivity of weakly coordinated palladacycles.

Angew Chem Int Ed Engl

Department of Chemistry, The Scripps Research Institute (TSRI), 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA) http://www.scripps.edu/chem/yu.

Published: January 2014

AI Article Synopsis

  • The text describes a new protocol for using palladium to selectively add deuterium to the ortho position of aromatic compounds like phenylacetic and benzoic acids.
  • This method provides a catalytic way to produce ortho-deuterated versions of these acids.
  • It highlights the differences in how palladacycle intermediates behave based on the strength of their chemical bonds during the reaction.

Article Abstract

We disclose a protocol for the palladium-catalyzed ortho-selective C-H deuteration of arenes. Phenylacetic acids and benzoic acids are suitable substrates for this reaction. This reaction offers a catalytic route to ortho-deuterated phenylacetic acids and benzoic acids and demonstrates the sharp difference in reactivity of palladacycle intermediates held together by weak and strong coordination.

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Source
http://dx.doi.org/10.1002/anie.201305388DOI Listing

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