Iridium‐Catalysed Cascade Synthesis of Oxindoles Using Diazo Compounds: A Quick Entry to C‐7‐Functionalized Oxindoles. Issue 19 (19th May 2017)

• Record Type: Journal Article
• Authors: Karmakar, Ujjwal; Das, Debapratim; Samanta, Rajarshi
• Is Part Of: European journal of organic chemistry. Issue 19(2017)
• Page Start: 2780
• Page End: 2788
• Publication Date: 2017-05-19
• Subjects: C‐H activation -- Nitrogen heterocycles -- Iridium -- Homogeneous catalysis -- Cyclization -- Cascade reactions; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201700214
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A cascade iridium‐catalysed oxindole synthesis was achieved using pyridyl‐protected anilines and bis(2, 2, 2‐trifluoroethyl) 2‐diazomalonate. The developed protocol is simple and scalable, and has a broad scope and excellent regioselectivity. The pyridyl directing group can easily be removed. The method was further extended to give C‐7‐functionalized oxindole derivatives in a straightforward manner. The role of bis(2, 2, 2‐trifluoroethyl) 2‐diazomalonate for oxindole preparation has been explored. Abstract : The iridium(III)‐catalysed cascade synthesis of oxindoles and its application to the synthesis of its C‐7‐functionalized congeners are described.