Open AccessRuthenium-Catalyzed C–H Arylation of Diverse Aryl Carboxylic Acids with Aryl and Heteroaryl Halides
Author(s) -
Liangbin Huang,
Daniel J. Weix
Publication year - 2016
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.6b02862
Subject(s) - chemistry , aryl , ruthenium , trifluoromethanesulfonate , carboxylate , iodide , electrophile , medicinal chemistry , ligand (biochemistry) , halide , bromide , carboxylic acid , catalysis , pyridine , amide , organic chemistry , alkyl , biochemistry , receptor
Ruthenium ligated to tricyclohexylphosphine or di-tert-butylbipyridine catalyzes the arylation of carboxylic acids with diverse aryl halides (iodide, bromide, and triflate; aryl and heteroaryl). In addition, arylations with 2-iodophenol formed benzochromenones, carboxylate was shown to be a stronger donor than an amide, and the arylation of a pyridine carboxylate was demonstrated. Stoichiometric studies demonstrated that the added ligand is required for reaction with the electrophile but not the C-H bond.