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Pii: S0040-4039(99)01757-8
| Content Provider | Semantic Scholar |
|---|---|
| Author | Gevorgyan, Vladimir Liu, Jian-Xiu Rubin, Michael Benson, Sharonda Yamamoto, Yoshinori |
| Copyright Year | 2003 |
| Abstract | The primary alcohols l a d and ethers 4a-b were effectively reduced into the corresponding hydrocarbons 2 by HSiEt3 in the presence of catalytic amounts of B(C6F5)3. The secondary alkyl ethers 4g,h underwent cleavage and/or reduction under similar reaction conditions to produce either the silyl ether 3k or the corresponding alcohol 5b upon subsequent deprotection with TBAF. The secondary alcohols (lg,h) and tertiary alcohol li, as well as tertiary alkyl ether 4i, did not react with the HSiEt3/(B(C6F5)3 reducing reagent at all. The following relative reactivity order of substrates was found: primary>>secondary>tertiary. The methyl aryl ethers 4c-e and alkyl aryl ether 4f were smoothly deprotected to give the corresponding silyl ethers 3b,h-j in nearly quantitative isolated yields. © 1999 Elsevier Science Ltd. All rights reserved. It is known that hydrosilanes are able to reduce alcohols and alkyl ethers in the presence of Lewis acids (Eq. 1). 1 These methods require at least stoichiometric amounts of Lewis acid. Furthermore, the methodologies described are most effective for the reduction of a C--O bond at tertiary carbon, l are much less effective for the reduction of secondary substrates, 2 and absolutely ineffective for the reduction of primary alcohols and ethers (Eq. 1). l I / R HSiRa/oxcoss-LA I ~ ' o , C H I R=H, AIkyl (1) |
| File Format | PDF HTM / HTML |
| Alternate Webpage(s) | http://chemistry.mdma.ch/hiveboard/picproxie_docs/000529479-Tet_Lett_40_Alcohol_reduction_with_triethylsilane_.pdf |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
