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Volumn 65, Issue 19, 2000, Pages 6179-6186

A novel B(C6F5)3-catalyzed reduction of alcohols and cleavage of aryl and alkyl ethers with hydrosilanes

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ALCOHOL; ALKYL ARYL ETHER; HYDROCARBON; SILANE DERIVATIVE;

EID: 0034703322     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000726d     Document Type: Article
Times cited : (296)

References (61)
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    • 3 system, see ref 3c.
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    • It is well-known that primary alcohols and ethers do not undergo reduction with traditional hydrosilane/Lewis acid reducing system; see refs 3 and 4
    • It is well-known that primary alcohols and ethers do not undergo reduction with traditional hydrosilane/Lewis acid reducing system; see refs 3 and 4.
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    • 3 system is absolutely opposite to the reactivity order which was observed in the reduction of alcohols by the classical methods; see refs 3 and 4 (eq 1)
    • 3 system is absolutely opposite to the reactivity order which was observed in the reduction of alcohols by the classical methods; see refs 3 and 4 (eq 1).
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    • 3 system
    • 3 system.
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    • 3, see ref 19.
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    • We used silyl ether 3k for investigation of isotope effect since the reduction of silyl ethers seems to be the slowest step in the overall transformation: alcohol → hydrocarbon (see Figure)
    • We used silyl ether 3k for investigation of isotope effect since the reduction of silyl ethers seems to be the slowest step in the overall transformation: alcohol → hydrocarbon (see Figure).
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    • S and that the secondary isotopic effect is negligible
    • S and that the secondary isotopic effect is negligible.
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    • Vigorous hydrogen emission was observed
    • Vigorous hydrogen emission was observed.
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    • We do not postulate an involvement of free silicenium cation in the proposed mechanism
    • We do not postulate an involvement of free silicenium cation in the proposed mechanism.
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    • 30 have been recently unambiguously demonstrated.
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    • Formation of 14 was confirmed by GC-MS analyses of the crude reaction mixtures
    • Formation of 14 was confirmed by GC-MS analyses of the crude reaction mixtures.
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    • Test experiments revealed that primary triethylsilyl ethers underwent reduction into the corresponding hydrocarbons 2
    • Test experiments revealed that primary triethylsilyl ethers underwent reduction into the corresponding hydrocarbons 2.
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    • 3
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    • Reuchardt, C.; Grundmeier, M. Chem. Ber. 1975, 108, 2448. For preparation of benzyl ethers, see, for example: Fukuzawa, A.; Sato, H.; Masamune, T. Tetrahedron Lett. 1987, 28, 4303.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.