Synthesis of Methanes Having Four Different Carbon Substituents Utilizing Indium-Catalyzed Cleavage of Carbon–Pyrrolyl Bonds

✍ Scribed by Teruhisa Tsuchimoto; Taku Ainoya; Kazuki Aoki; Tatsuya Wagatsuma; Eiji Shirakawa

• Publisher: John Wiley and Sons
• Year: 2009
• Tongue: English
• Weight: 303 KB
• Volume: 2009
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200900246

✦ Synopsis

Abstract

A pyrrolyl group bound to an sp^3^ carbon atom in gem‐dipyrrolylalkanes was found to be successfully replaced by a certain range of carbon nucleophiles in the presence of an indium catalyst. The reaction can also be performed efficiently as a three‐component assembly of alkynes, pyrroles, and carbon nucleophiles in one batch. The strategy is highly useful to synthesize methanes having four different carbon substituents. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)