A direct route to six and seven membered lactones via γ-C(sp3)–H activation: a simple protocol to build molecular complexity |
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Authors: | Jayabrata Das Pravas Dolui Wajid Ali Jyoti Prasad Biswas Hediyala B Chandrashekar Gaurav Prakash Debabrata Maiti |
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Institution: | Department of Chemistry, IIT Bombay, Powai, Mumbai 400076 India.; Tokyo Tech World Research Hub Initiative(WRHI), Laboratory for Chemistry and Life Science, Tokyo Institute of Technology, Tokyo 152-8550 Japan |
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Abstract: | Lactones comprise a class of valuable compounds having biological as well as industrial importance. Development of a methodology to synthesize such molecules directly from readily available materials such as aliphatic carboxylic acid is highly desirable. Herein, we have reported synthesis of δ-lactones and ε-lactones via selective γ-C(sp3)–H activation. The γ-C–H bond containing aliphatic carboxylic acids provide six or seven membered lactones depending on the olefin partner in the presence of a palladium catalyst. A mechanistic investigation suggests that C–H activation is the rate-determining step. Further transformations of the lactones have been carried out to showcase the applicability of the present strategy.Six and seven membered lactones have been synthesized directly from readily available aliphatic acids. |
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