title: Palladium-catalyzed ortho-selective C-H deuteration of arenes: evidence for superior reactivity of weakly coordinated palladacycles.
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.
authors.affiliation: Department of Chemistry, The Scripps Research Institute (TSRI), 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA) http://www.scripps.edu/chem/yu.
authors.forename: Sandy
authors.initials: S
authors.lastname: Ma
authors.forename: Giorgio
authors.initials: G
authors.lastname: Villa
authors.forename: Peter S
authors.initials: PS
authors.lastname: Thuy-Boun
authors.forename: Anna
authors.initials: A
authors.lastname: Homs
authors.forename: Jin-Quan
authors.initials: JQ
authors.lastname: Yu
mesh_terms: D001565:Benzoates / Q000737:chemistry; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D003903:Deuterium / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D010648:Phenylacetates / Q000737:chemistry*
chemical_list: D001565:Benzoates; D010648:Phenylacetates; D010165:Palladium; D002244:Carbon; D006859:Hydrogen; D003903:Deuterium
keywords: CH activation; deuteration; palladium; phenylacetic acids; weak coordination