An In(III)/Si catalyst system effects the direct allyl substitution of alcohols and silyl ethers under mild conditions. A deoxygenation of alcohols is also promoted by InCl3 catalyst. This method requires no pretreatment or protection of hydroxy groups or deprotection of siloxy groups. The completion of the catalytic allylation depends on the low oxophilicity and high halophilicity of In(III) halide species, and other representative Lewis acids such as AlCl3 and BF3 have no catalytic activity for the allylations. The oxophilicity and halophilicity are also demonstrated by NMR studies.
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Pure and Applied Chemistry
The Scientific Journal of IUPAC
Ed. by Burrows, Hugh / Stohner, Jürgen
12 Issues per year
IMPACT FACTOR 2016: 2.626
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CiteScore 2017: 3.42
SCImago Journal Rank (SJR) 2017: 1.212
Source Normalized Impact per Paper (SNIP) 2017: 1.546
- Online
- ISSN
- 1365-3075
Reaction of alcohols and silyl ethers in the presence of an indium/silicon-based catalyst system: Deoxygenation and allyl substitution
Akio Baba / Makoto Yasuda / Yoshihiro Nishimoto / Takahiro Saito / Yoshiyuki Onishi
Published Online: 2009-01-01 | DOI: https://doi.org/10.1351/pac200880050845
Free Access
Keywords: alcohol; combined system; direct substitution; indium; silicon; silyl ether
Conference
International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-14), International Symposium on Organometallic Chemistry Directed Toward Organic Synthesis, OMCOS, Organometallic Chemistry Directed Toward Organic Synthesis, 14th, Nara, Japan, 2007-08-02–2007-08-06
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About the article
Published Online: 2009-01-01
Published in Print: 2008-01-01
Citation Information: Pure and Applied Chemistry, Volume 80, Issue 5, Pages 845–854, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1351/pac200880050845.
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