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

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Nickelocene as an Air- and Moisture-Tolerant Precatalyst in the Regioselective Synthesis of Multisubstituted Pyridines

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Title
Nickelocene as an Air- and Moisture-Tolerant Precatalyst in the Regioselective Synthesis of Multisubstituted Pyridines
Author
Cho, Il YoungKim, Woo GyumJeon, Ji HwanLee, Jeong WooSeo, Jeong KonSeo, JongcheolHong, Sung You
Issue Date
2021-07
Publisher
AMER CHEMICAL SOC
Citation
JOURNAL OF ORGANIC CHEMISTRY, v.86, no.14, pp.9328 - 9343
Abstract
Ni(COD)(2) -catalyzed cycloaddition reactions to access pyridines have been extensively studied. However, this catalyst typically requires drying procedures and inert-atmosphere techniques for the reactions. Herein, we report operationally simple nickel(0) catalysis to access substituted pyridines from various nitriles and 1,6-diynes without the aid of air-free techniques. The Ni-Xantphos-based catalytic manifold is tolerant to air, moisture, and heat while promoting the [2 + 2 + 2] cycloaddition reactions with high reaction yields and broad substrate scope. In addition, we disclose that not only the steric effect but also the frontier molecular orbital interactions can play a critical role in determining the regiochemical outcome of nickel-catalyzed [2 + 2 + 2] cycloaddition for the synthesis of substituted pyridines.
URI
https://scholarworks.unist.ac.kr/handle/201301/53254
URL
https://pubs.acs.org/doi/10.1021/acs.joc.1c00577
DOI
10.1021/acs.joc.1c00577
ISSN
0022-3263
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CHM_Journal Papers
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