A novel reduction of alcohols and ethers with a HSiEt3/catalytic B(C6F5)3 system

Vladimir Gevorgyan; Jian Xiu Liu; Michael Rubin; Sharonda Benson; Yoshinori Yamamoto

doi:10.1016/S0040-4039(99)01757-8

A novel reduction of alcohols and ethers with a HSiEt₃/catalytic B(C₆F₅)₃ system

Vladimir Gevorgyan, Jian Xiu Liu, Michael Rubin, Sharonda Benson, Yoshinori Yamamoto

Research output: Contribution to journal › Article › peer-review

174 Scopus citations

Abstract

The primary alcohols 1a-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 (1g,h) and tertiary alcohol 1i, 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.

Original language	English (US)
Pages (from-to)	8919-8922
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	50
DOIs	https://doi.org/10.1016/S0040-4039(99)01757-8
State	Published - Dec 10 1999
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "A novel reduction of alcohols and ethers with a HSiEt3/catalytic B(C6F5)3 system",

abstract = "The primary alcohols 1a-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 (1g,h) and tertiary alcohol 1i, 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.",

author = "Vladimir Gevorgyan and Liu, {Jian Xiu} and Michael Rubin and Sharonda Benson and Yoshinori Yamamoto",

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T1 - A novel reduction of alcohols and ethers with a HSiEt3/catalytic B(C6F5)3 system

AU - Gevorgyan, Vladimir

AU - Liu, Jian Xiu

AU - Rubin, Michael

AU - Benson, Sharonda

AU - Yamamoto, Yoshinori

PY - 1999/12/10

Y1 - 1999/12/10

N2 - The primary alcohols 1a-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 (1g,h) and tertiary alcohol 1i, 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.

AB - The primary alcohols 1a-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 (1g,h) and tertiary alcohol 1i, 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.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 50

ER -

A novel reduction of alcohols and ethers with a HSiEt₃/catalytic B(C₆F₅)₃ system

Abstract

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