Synthesis of Thioethers by InI3-Catalyzed Substitution of Siloxy Group Using Thiosilanes
1
Frontier Research Base for Global Young Researchers, Center for Open Innovation Research and Education(COiRE), Graduate School of Engineering, Osaka University, Osaka 565-0871, Japan
2
Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Osaka 565-0871, Japan
*
Authors to whom correspondence should be addressed.
Molecules 2016, 21(10), 1330; https://doi.org/10.3390/molecules21101330
Received: 6 September 2016
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Accepted: 3 October 2016
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Published: 6 October 2016
(This article belongs to the Special Issue Advances in Silicon Chemistry)
The substitution of a siloxy group using thiosilanes smoothly occurred in the presence of InI3 catalyst to yield the corresponding thioethers. InI3 was a specifically effective catalyst in this reaction system, while other typical Lewis acids such as BF3⋅OEt2, AlCl3, and TiCl4 were ineffective. Various silyl ethers such as primary alkyl, secondary alkyl, tertiary alkyl, allylic, benzylic, and propargylic types were applicable. In addition, bulky OSitBuMe2 and OSiiPr3 groups, other than the OSiMe3 group, were successfully substituted. The substitution reaction of enantiopure secondary benzylic silyl ether yielded the corresponding racemic thioether product, which suggested that the reaction of tertiary alkyl, secondary alkyl, benzylic, and propargylic silyl ethers would proceed via a SN1 mechanism.
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Keywords:
indium; silyl ethers; thiosilanes; thioethers
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MDPI and ACS Style
Nishimoto, Y.; Okita, A.; Baba, A.; Yasuda, M. Synthesis of Thioethers by InI3-Catalyzed Substitution of Siloxy Group Using Thiosilanes. Molecules 2016, 21, 1330. https://doi.org/10.3390/molecules21101330
AMA Style
Nishimoto Y, Okita A, Baba A, Yasuda M. Synthesis of Thioethers by InI3-Catalyzed Substitution of Siloxy Group Using Thiosilanes. Molecules. 2016; 21(10):1330. https://doi.org/10.3390/molecules21101330
Chicago/Turabian StyleNishimoto, Yoshihiro, Aya Okita, Akio Baba, and Makoto Yasuda. 2016. "Synthesis of Thioethers by InI3-Catalyzed Substitution of Siloxy Group Using Thiosilanes" Molecules 21, no. 10: 1330. https://doi.org/10.3390/molecules21101330
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