Reductive coupling of allenyl/allyl carbonate with alkyne under dual cobalt-photoredox catalysis

Subhankar Pradhan, Dhananjay Satav, Sayan Dutta, Bholanath Maity, Luigi Cavallo () and Basker Sundararaju ()
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Subhankar Pradhan: Indian Institute of Technology Kanpur
Dhananjay Satav: Indian Institute of Technology Kanpur
Sayan Dutta: King Abdullah University of Science and Technology (KAUST)
Bholanath Maity: King Abdullah University of Science and Technology (KAUST)
Luigi Cavallo: King Abdullah University of Science and Technology (KAUST)
Basker Sundararaju: Indian Institute of Technology Kanpur

Nature Communications, 2024, vol. 15, issue 1, 1-16

Abstract: Abstract Skipped dienes are among the most prevalent motifs in a vast array of natural products, medicinal compounds, and fatty acids. Herein, we disclose a straightforward one-step reductive protocol under Co/PC for the synthesis of diverse 1,4-dienes with excellent regio- and stereoselectivity. The protocol employs allenyl or allyl carbonate as π-allyl source, allowing for the direct synthesis of skipped diene with a broad range of alkynes including terminal alkynes, propargylic alcohols, and internal alkynes. The method also demonstrated the biomimetic homologation of natural terpenols into synthetic counterparts via iterative allylation of three-carbon allyl units, employing propargylic alcohol as a readily available alkyne source. Experimental studies, control experiments, and DFT calculations suggest the dual catalytic process generates 1,3-diene from allenyl carbonate, followed by proton and electron transfer leading to Co(II)-π-allyl species prior to the alkyne coupling. The catalytic cycle transitions through Co(II), Co(I), and Co(III).

Date: 2024
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DOI: 10.1038/s41467-024-54718-9

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