A direct route to six and seven membered lactones γ-C(sp)-H activation: a simple protocol to build molecular complexity

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-lacto...

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Veröffentlicht in:Chemical science (Cambridge) 2020-09, Vol.11 (35), p.9697-972
Hauptverfasser: Das, Jayabrata, Dolui, Pravas, Ali, Wajid, Biswas, Jyoti Prasad, Chandrashekar, Hediyala B, Prakash, Gaurav, Maiti, Debabrata
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Sprache:eng
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Zusammenfassung: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 -lactones via selective γ-C(sp 3 )-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.
ISSN:2041-6520
2041-6539
DOI:10.1039/d0sc03144e