title: Hydroarylation of arynes catalyzed by silver for biaryl synthesis.
abstract: A new biaryl synthesis via silver-catalyzed hydroarylation of arynes from acyclic building blocks with unactivated arenes in intra- and intermolecular manners has been developed. The previously observed Diels-Alder reactions of arynes with arene were not observed under the current silver-catalyzed conditions. Deuterium scrambling and DFT calculations suggest a stepwise electrophilic aromatic substitution mechanism through the formation of a Wheland-type intermediate followed by a water-catalyzed proton transfer in the final step of the hydroarylation.
authors.affiliation: Department of Chemistry, University of Illinois at Chicago , 845 West Taylor Street, Chicago, Illinois 60607, United States.
authors.forename: Nam-Kyu
authors.initials: NK
authors.lastname: Lee
authors.forename: Sang Young
authors.initials: SY
authors.lastname: Yun
authors.forename: Phani
authors.initials: P
authors.lastname: Mamidipalli
authors.forename: Ryan M
authors.initials: RM
authors.lastname: Salzman
authors.forename: Daesung
authors.initials: D
authors.lastname: Lee
authors.forename: Tao
authors.initials: T
authors.lastname: Zhou
authors.forename: Yuanzhi
authors.initials: Y
authors.lastname: Xia
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011789:Quantum Theory; D012834:Silver / Q000737:chemistry*
chemical_list: D000480:Alkynes; D006841:Hydrocarbons, Aromatic; D012834:Silver