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Hong, Sung You
Synthetic Organic Chemistry Laboratory
Research Interests
  • Synthetic organic chemistry, transition metals, oxidation state

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Synthesis of α,β-unsaturated ketones through nickel-catalysed aldehyde-free hydroacylation of alkynes

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Title
Synthesis of α,β-unsaturated ketones through nickel-catalysed aldehyde-free hydroacylation of alkynes
Author
Rhlee, Joon HoSaikat, MaitiLee, Jeong WooLee, Ho SeungBakhtiyorzoda, Ismoili AhrorLee, SoochanPark, JaehyunKang, Seok JuKim, Yung SamSeo, Jeong KonMyung, KyungjaeChoe, WonyoungHong, Sung You
Issue Date
2022-02
Publisher
NATURE PUBLISHING GROUP
Citation
COMMUNICATIONS CHEMISTRY, v.5, no.1, pp.13
Abstract
α,β-Unsaturated ketones are common feedstocks for the synthesis of fine chemicals, pharmaceuticals, and natural products. Transition metal-catalysed hydroacylation reactions of alkynes using aldehydes have been recognised as an atom-economical route to access α,β-unsaturated ketones through chemoselective aldehydic C–H activation. However, the previously reported hydroacylation reactions using rhodium, cobalt, or ruthenium catalysts require chelating moiety-bearing aldehydes to prevent decarbonylation of acyl-metal-hydride complexes. Herein, we report a nickel-catalysed anti-Markovnikov selective coupling process to afford non-tethered E-enones from terminal alkynes and S-2-pyridyl thioesters in the presence of zinc metal as a reducing agent. Utilization of a readily available thioester as an acylating agent and water as a proton donor enables the mechanistically distinctive and aldehyde-free hydroacylation of terminal alkynes. This non-chelation-controlled approach features mild reaction conditions, high step economy, and excellent regio- and stereoselectivity.
URI
https://scholarworks.unist.ac.kr/handle/201301/57156
URL
https://www.nature.com/articles/s42004-022-00633-3
DOI
10.1038/s42004-022-00633-3
ISSN
2399-3669
Appears in Collections:
CHM_Journal Papers
ECHE_Journal Papers
BME_Journal Papers
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