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Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
Published on: August 1, 2018
Photochemical Branched Hydrothiocarbonylation of Vinyl Arenes with DHP-Thioesters
Amit Pal1, Sandip Bag1, Sariga Mangalamundackal Vijayan1
1School of Chemistry, Indian Institute of Science Education and Research Thiruvananthapuram, Thiruvananthapuram - 695551, Kerala, India.
Abstract:
We describe for the first time a photochemical branched hydrothiocarbonylation of vinyl arenes with bench-stable 1,4-dihydropyridine thioesters to furnish various thioesters in high regioselectivity. 4CzIPN assists in the activation of DHP-thioester precursors. The Pd/phosphine catalyst system plays a role in harnessing reactivity and achieving site-selectivity. In this mild and scalable method, various thioesters can be obtained with good functional group tolerance, including late-stage thioesterification to deliver drug-conjugates. A branched hydroselenocarbonylation of styrene is also achieved with DHP-selenoester to afford the selenoester.
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