Tandem dehydrogenation-olefination-decarboxylation of cycloalkyl carboxylic acids via multifold C–H activation

Tanay Pal, Premananda Ghosh, Minhajul Islam, Srimanta Guin, Suman Maji, Suparna Dutta, Jayabrata Das, Haibo Ge () and Debabrata Maiti ()
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Tanay Pal: Indian Institute of Technology Bombay
Premananda Ghosh: Indian Institute of Technology Bombay
Minhajul Islam: Indian Institute of Technology Bombay
Srimanta Guin: Indian Institute of Technology Bombay
Suman Maji: Indian Institute of Technology Bombay
Suparna Dutta: Indian Institute of Technology Bombay
Jayabrata Das: Indian Institute of Technology Bombay
Haibo Ge: Texas Tech University
Debabrata Maiti: Indian Institute of Technology Bombay

Nature Communications, 2024, vol. 15, issue 1, 1-14

Abstract: Abstract Dehydrogenation chemistry has long been established as a fundamental aspect of organic synthesis, commonly encountered in carbonyl compounds. Transition metal catalysis revolutionized it, with strategies like transfer-dehydrogenation, single electron transfer and C–H activation. These approaches, extended to multiple dehydrogenations, can lead to aromatization. Dehydrogenative transformations of aliphatic carboxylic acids pose challenges, yet engineered ligands and metal catalysis can initiate dehydrogenation via C–H activation, though outcomes vary based on substrate structures. Herein, we have developed a catalytic system enabling cyclohexane carboxylic acids to undergo multifold C–H activation to furnish olefinated arenes, bypassing lactone formation. This showcases unique reactivity in aliphatic carboxylic acids, involving tandem dehydrogenation-olefination-decarboxylation-aromatization sequences, validated by control experiments and key intermediate isolation. For cyclopentane carboxylic acids, reluctant to aromatization, the catalytic system facilitates controlled dehydrogenation, providing difunctionalized cyclopentenes through tandem dehydrogenation-olefination-decarboxylation-allylic acyloxylation sequences. This transformation expands carboxylic acids into diverse molecular entities with wide applications, underscoring its importance.

Date: 2024
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DOI: 10.1038/s41467-024-49359-x

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