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Saikat, Maiti
유전체 항상성 연구단
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Synthesis of alpha,beta-unsaturated ketones through nickel-catalysed aldehyde-free hydroacylation of alkynes

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Title
Synthesis of alpha,beta-unsaturated ketones through nickel-catalysed aldehyde-free hydroacylation of alkynes
Author(s)
Rhlee, Joon Ho; Saikat Maiti; Lee, Jeong Woo; Lee, Ho Seung; Bakhtiyorzoda, Ismoili Ahror; Lee, Soochan; Park, Jaehyun; Kang, Seok Ju; Kim, Yung Sam; Seo, Jeong Kon; Kyungjae Myung; Choe, Wonyoung; Hong, Sung You
Publication Date
2022-02
Journal
Communications Chemistry, v.5, no.1
Publisher
NATURE PUBLISHING GROUP
Abstract
Transition metal-catalysed hydroacylation of alkynes using aldehydes is an atom-economical route to access alpha,beta-unsaturated ketones, but typically requires aldehydes that bear chelating moieties. Here, the authors report a nickel-catalysed anti-Markovnikov selective coupling process to afford non-tethered E-enones from terminal alkynes and S-2-pyridyl thioesters. alpha,beta-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 alpha,beta-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://pr.ibs.re.kr/handle/8788114/12959
DOI
10.1038/s42004-022-00633-3
ISSN
2399-3669
Appears in Collections:
Center for Genomic Integrity(유전체 항상성 연구단) > 1. Journal Papers (저널논문)
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