Journal of Organic Chemistry p. 1285 - 1294 (2016)
Update date:2022-08-04
Topics:
Smyth, Lynette A.
Phillips, Eric M.
Chan, Vincent S.
Napolitano, José G.
Henry, Rodger
Shekhar, Shashank
A novel method for Pd-catalyzed triflination of aryl and heteroaryl triflates using NaSO2CF3 as the nucleophile is described. The combination of Pd2(dba)3 and RockPhos formed the most effective catalyst. A broad range of functional groups and heteroaromatic compounds were tolerated under the neutral reaction conditions. The order of reactivity ArOTf ≥ ArCl ≥ ArBr is consistent with transmetalation being a slow step of the reaction.
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