Direct Access to Aryl Bis(trifluoromethyl)carbinols from Aryl Bromides or Fluorosulfates: Palladium‐Catalyzed Carbonylation

Abstract

Ap alladium-catalyzed carbonylative approachf or the direct conversion of (hetero)aryl bromides into their a,abis(trifluoromethyl)carbinols is described, and it employs only stoichiometric amounts of carbon monoxide and trifluoromethyltrimethylsilane.I na ddition, aryl fluorosulfates proved highly compatible with these reaction conditions.T he method is tolerant of ad iverse set of functional groups,a nd it is adaptable to late-stage carbon-isotope labeling. Conflict of interestTr oels Skrydstrup is ac o-owner of SyTracks a/s,w hich commercializes COgen and the two-chamber technology.

Ex situ gas generation for lab scale organic synthesis

“…Several reports have since appeared which use this method to prepare aryl fluorosulfate starting materials, and engage them in a subsequent reaction step. [110][111][112][113][114][115] However, also novel, SO2F2-mediated methodological explorations have made use of the ex situ gas production. The Sammis group in late 2018 published the trifluoroethylation of amines, by intermediacy of trifluoroethyl fluorosulfate (Scheme 15).…”