Catalyst‐Free Indirect C−F Activation of 3‐Perfluoroalkyl Indoles. Issue 38 (10th October 2022)

• Record Type: Journal Article
• Authors: Roider, Thomas; Kleykamp, Olaf A.; Ivlev, Sergei I.; Hoffmann, Reinhard W.; Tallarek, Ulrich
• Is Part Of: European journal of organic chemistry. Volume 2022:Issue 38(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-10-10
• Subjects: Catalyst-free -- Flow chemistry -- Indirect C−F Activation -- Photochemistry; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202201025
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: We present a catalyst‐free method for indirect C−F activation of a perfluorinated side chain in C(3) position of 1 H ‐indoles with moderate to good yields, which allows the introduction of a nucleophile at the α ‐CF2 ‐group of the perfluorinated chain. By adapting this approach, it is also possible to modify 3‐perfluorobutyl‐2‐phenyl‐1 H ‐indole to generate privileged structures for medicinal chemistry. Abstract : A method for activating the α ‐CF2 ‐group of 3‐perfluorobutyl‐1 H ‐indoles without catalyst is presented, enabling the preparation of fluorine‐containing 3‐substituted‐2‐phenylindoles, which are preferred structures for medicinal chemistry.