Mechanochemical Conversion of Aromatic Amines to Aryl Trifluoromethyl Ethers.

ABSTRACT: Increased interest in the trifluoromethoxy group in organic synthesis and medicinal chemistry has induced a demand for new, selective, general, and faster methods applicable to natural products and highly functionalized compounds at a later stage of hit-to-lead campaigns. Applying pyrylium tetrafluoroborate, we have developed a mechanochemical protocol to selectively substitute the aromatic amino group with the OCF₃ functionality. The scope of our method includes 31 examples of ring-substituted anilines, including amides and sulfonamides. Expected S_NAr products were obtained in excellent yields. The presented concise method opens a pathway to new chemical spaces for the pharmaceutical industry.

SUBMITTER: Jakubczyk M 

PROVIDER: S-EPMC9204773 | biostudies-literature | 2022 Jun

REPOSITORIES: biostudies-literature