Divergent Reactivity in Palladium‐Catalyzed Annulation with Diarylamines and α,β‐Unsaturated Acids: Direct Access to Substituted 2‐Quinolinones and Indoles |
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Authors: | Dr Rajesh Kancherla Togati Naveen Prof Debabrata Maiti |
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Institution: | Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai‐400076 (India) |
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Abstract: | A palladium‐catalyzed C?H activation strategy has been successfully employed for exclusive synthesis of a variety of 3‐substituted indoles. A 3+3] annulation for synthesizing substituted 2‐quinolinones was recently developed by reaction of α,β‐unsaturated carboxylic acids with diarylamines under acidic conditions. In the present work, an analogous 3+2] annulation is achieved from the same set of starting materials under basic conditions to generate 1,3‐disubstituted indoles exclusively. Mechanistic studies revealed an ortho‐palladation–π‐coordination–β‐migratory insertion–β‐hydride elimination reaction sequence to be operative under the reaction conditions. |
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Keywords: | amines carboxylic acids C H activation indoles palladium |
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