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나노물질 및 화학반응 연구단
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Correlation between Functionality Preference of Ru Carbenes and exo/endo Product Selectivity for Clarifying the Mechanism of Ring-closing Enyne Metathesis

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Title
Correlation between Functionality Preference of Ru Carbenes and exo/endo Product Selectivity for Clarifying the Mechanism of Ring-closing Enyne Metathesis
Author(s)
Lee, Ok Suk; Kyung Hwan Kim; Kim, Jinwoo; Kwon, Kuktae; Ok, Taedong; Hyot Cherl Ihee; Lee, Hee-Yoon; Sohn, Jeong-Hun
Publication Date
2013-09
Journal
JOURNAL OF ORGANIC CHEMISTRY, v.78, no.17, pp.8242 - 8249
Publisher
AMER CHEMICAL SOC
Abstract
Functionality preferences of metathesis Ru carbenes to various alkenes and alkynes with electronic and steric diversity were determined by using time-dependent fluorescence quenching. The functionality preferences depend not only on the properties of multiple bonds but also on the ligands on Ru. There was a good correlation between functionality preference and the metathesis reaction outcome. The correlation between functionality preference and exo/endo product ratio offers a solution to resolve the mechanistic issue related with alkene- vs alkyneinitiated pathway in ring-closing enyne metathesis. The correlation indicates the preference is likely to dictate the reaction pathway and eventually the outcome of the reaction. The Ru catalyst favoring alkyne over alkene provides more endo product, indicating that the reaction mainly initiates at the alkyne. By changing the substitution pattern, the preference can be reversed to give an exclusive exo product.
URI
https://pr.ibs.re.kr/handle/8788114/1574
ISSN
0022-3263
Appears in Collections:
Center for Nanomaterials and Chemical Reactions(나노물질 및 화학반응 연구단) > Journal Papers (저널논문)
Files in This Item:
34_IBS CA1301-1_JOC_166-01-3-19_Correlation between Functionality Preference of Ru Carbenes and.pdfDownload

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