PFOA‐Catalyzed Regioselective Alkylation of Indolylmethanols with 2‐Alkylazaarenes**

Abstract

The selective alkylation of 2‐indolylmethanols with 2‐methyl‐N‐heteroaromatics in the presence of perfluorooctanoic acid is herein demonstrated. This protocol features high regioselectivity, easy availability of raw materials and well tolerance of functional groups. This approach allows the formation of a range of hindered quaternary centers. More importantly, the present method offers efficient ways to introduce biologically important indole and quinoline skeleton into highly complex molecular.

Regioselective Reaction of 2-Indolylmethanols with Enamides

“…On the other hand, 2-indolylmethanols can also transform into carbocations, vinyliminium and delocalized cations in the presence of a Lewis or Brønsted acid to participate in various substitution reactions. In this context, various nucleophiles include indoles and electron-rich heterocycles [29][30][31][32], naphthol [33], phosphines [34,35], thiophenols [36], tryptamines and tryptophols [37], sodium sulfinates [38], aldehydes [39], vinyl silyl ethers [40], 2-alkyazaarenes [41], azlactones [42], prazol-5ones [43], anhydrides and cyclic enaminoes [44,45] and guaiazulenes [46] and have been applied in the substitution of 2-indolylmethanols either at the C3 position or benzyl position. Nevertheless, the design and development of efficient, atom-economical and practical approaches are still needed to generate biologically important indole-containing compounds.…”