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Study on Pyridine-Boryl Radical-Promoted, Ketyl Radical-Mediated Carbon-Carbon Bond-Forming Reactions

Title
Study on Pyridine-Boryl Radical-Promoted, Ketyl Radical-Mediated Carbon-Carbon Bond-Forming Reactions
Author(s)
Jo, JunhyukKim, SomiPark, SeonyoungKim, SeonyulLee, SunggiChoi, Jun-HoChung, Won-jin
Issued Date
2024-06
Citation
The Journal of Organic Chemistry, v.89, no.12, pp.8985 - 9000
Type
Article
Keywords
COUPLING REACTIONSELECTRON-TRANSFERDENSITY FUNCTIONALSCH/PI INTERACTIONBORONATE ESTERSKETONESALDEHYDESMETALDERIVATIVESCYCLIZATION
ISSN
0022-3263
Abstract
Ketyl radicals are synthetically versatile reactive species, but their applications have been hampered by harsh generation conditions employing highly reducing metals. Recently, the pyridine-boryl radical received wide attention as a promising organic reductant because of its mildness as well as convenience in handling. While probing the utility of the pyridine-boryl radical, our group observed facile pinacol coupling reactivity that had not been known at that time. This serendipitous finding was successfully rendered into a practical synthesis of tetraaryl-1,2-diols in up to 99% yield within 1 h. Subsequently, upon examinations of various reaction manifolds, a diastereoselective ketyl-olefin cyclization was accomplished to produce cycloalkanols such as trans-2-alkyl-1-indanols. Compared to the previous methods, the stereocontrolling ability was considerably enhanced by taking advantage of the structurally modifiable boryl group that would be present near the bond-forming site. In this full account, our synthetic efforts with the O-boryl ketyl radicals are disclosed in detail, covering the discovery, optimization, scope expansion, and mechanistic analysis, including density functional theory (DFT) calculations. © 2024 American Chemical Society
URI
http://hdl.handle.net/20.500.11750/57155
DOI
10.1021/acs.joc.4c00946
Publisher
American Chemical Society
Related Researcher
  • 이성기 Lee, Sunggi
  • Research Interests Organic synthesis; Catalyst development; Reaction development; Radical chemistry; Stereoselective reaction
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Department of Physics and Chemistry Organic Synthesis & Catalysis Lab 1. Journal Articles

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