Palladium‐Catalyzed C‐N Bond Formation: A Straightforward Alkoxymethylation Process for the Synthesis of the C1 and C3‐Dialkoxy Indoles

Abstract

A novel approach for the synthesis of the C1 and C3‐dialkoxy indoles has been developed for using 2‐(phenylethynyl)aniline with formaldehyde and alcohols under the catalysis of acid and palladium acetate. This multicomponent reaction that provides a straightforward alkoxymethylation process to construct substituted indoles is expected to be an important method for the synthesis of indole derivatives.

Iodine-catalyzed cyclization–allylation of N-allyl-2-alkynylanilines via an iodocyclization–rearrangement–deiodination sequence

“…2 This method can be applied to cyclization-functionalization reactions of N , N -disubstituted o -alkynylanilines, which produce indoles with the migration of various substituents on the nitrogen to the 3-position (Y = NR, E = allyl, 3 acyl, 4 alkenyl, 5 etc. 6,7 ), as well as the reactions of oxygen 3 b , g ,5 b and sulfur analogues (Y = O and S). 8 Recently, metal-free reactions of N , N -disubstituted o -alkynylanilines with the 1,3-migration of carbon-based functional groups have been developed from the viewpoint of green and sustainable chemistry.…”

Lewis Acid-Promoted Three-Component Cyclization for the Construction of Functionalized Oxazoles

“…In continuation of our research interest in the field of transition metal-catalyzed MCRs, we recently reported an efficient and straightforward strategy for the synthesis of functionalized thiazoles from thioamides, ynals, and alcohols via three-component cyclization . On the basis of this work, we envisioned that oxazoles might be accessed through such a cyclization using Lewis acid as a catalyst.…”