Dehydrocoupling reactions of amines with silanes catalyzed by [(Et2N)3U][BPh4]

Jia Xi Wang; Aswini K. Dash; Jean Claude Berthet; Michel Ephritikhine; Moris S. Eisen

doi:10.1016/S0022-328X(00)00410-1

Dehydrocoupling reactions of amines with silanes catalyzed by [(Et₂N)₃U][BPh₄]

Jia Xi Wang, Aswini K. Dash, Jean Claude Berthet, Michel Ephritikhine, Moris S. Eisen^*

^*Corresponding author for this work

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

60 Scopus citations

Abstract

Dehydrocoupling reactions of primary amines RNH₂ with PhSiH₃ were catalyzed by [(Et₂N)₃U][BPh₄] to give the corresponding aminosilanes PhSiH_3-n(NHR)_n (n = 1-3), the relative yields of the products were found to be dependent on the experimental conditions and on the nature of R. For a primary silane (PhSiH₃), the reactivity of RNH₂ follows the order primary > secondary > tertiary. Similar dehydrocoupling reactions using secondary amines with secondary silanes were found to be less reactive. Homodehydrocoupling of the silane was found not to be a competing reaction at room temperature. The hydride [(RNH)₂UH][BPh₄], which is plausibly formed in the reaction of [(RNH)₃U][BPh₄] with PhSiH₃ is a likely intermediate in the catalytic cycle.

Original language	English
Pages (from-to)	49-57
Number of pages	9
Journal	Journal of Organometallic Chemistry
Volume	610
Issue number	1-2
DOIs	https://doi.org/10.1016/S0022-328X(00)00410-1
State	Published - 22 Sep 2000
Externally published	Yes

Keywords

Amines
Cationic
Dehydrocoupling
Silanes
Uranium

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10.1016/S0022-328X(00)00410-1

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@article{95ebde752fa9491f908a709ace153332,

title = "Dehydrocoupling reactions of amines with silanes catalyzed by [(Et2N)3U][BPh4]",

abstract = "Dehydrocoupling reactions of primary amines RNH2 with PhSiH3 were catalyzed by [(Et2N)3U][BPh4] to give the corresponding aminosilanes PhSiH3-n(NHR)n (n = 1-3), the relative yields of the products were found to be dependent on the experimental conditions and on the nature of R. For a primary silane (PhSiH3), the reactivity of RNH2 follows the order primary > secondary > tertiary. Similar dehydrocoupling reactions using secondary amines with secondary silanes were found to be less reactive. Homodehydrocoupling of the silane was found not to be a competing reaction at room temperature. The hydride [(RNH)2UH][BPh4], which is plausibly formed in the reaction of [(RNH)3U][BPh4] with PhSiH3 is a likely intermediate in the catalytic cycle.",

keywords = "Amines, Cationic, Dehydrocoupling, Silanes, Uranium",

author = "Wang, {Jia Xi} and Dash, {Aswini K.} and Berthet, {Jean Claude} and Michel Ephritikhine and Eisen, {Moris S.}",

note = "Funding Information: A.K.D. thanks the Technion for a Postdoctoral Fellowship. M.E. and M.S.E. thanks the Israel Ministry of Sciences and the French Minist{\`e}re des Affaires Etrang{\`e}res for funding the Arc en Ciel/Keshet Project No 50. This research was supported by the Henri Gutwirth Fund for the Promotion of Research at the Technion and by the Technion V.P.R. Fund.",

year = "2000",

month = sep,

day = "22",

doi = "10.1016/S0022-328X(00)00410-1",

language = "英语",

volume = "610",

pages = "49--57",

journal = "Journal of Organometallic Chemistry",

issn = "0022-328X",

publisher = "Elsevier",

number = "1-2",

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TY - JOUR

T1 - Dehydrocoupling reactions of amines with silanes catalyzed by [(Et2N)3U][BPh4]

AU - Wang, Jia Xi

AU - Dash, Aswini K.

AU - Berthet, Jean Claude

AU - Ephritikhine, Michel

AU - Eisen, Moris S.

N1 - Funding Information: A.K.D. thanks the Technion for a Postdoctoral Fellowship. M.E. and M.S.E. thanks the Israel Ministry of Sciences and the French Ministère des Affaires Etrangères for funding the Arc en Ciel/Keshet Project No 50. This research was supported by the Henri Gutwirth Fund for the Promotion of Research at the Technion and by the Technion V.P.R. Fund.

PY - 2000/9/22

Y1 - 2000/9/22

N2 - Dehydrocoupling reactions of primary amines RNH2 with PhSiH3 were catalyzed by [(Et2N)3U][BPh4] to give the corresponding aminosilanes PhSiH3-n(NHR)n (n = 1-3), the relative yields of the products were found to be dependent on the experimental conditions and on the nature of R. For a primary silane (PhSiH3), the reactivity of RNH2 follows the order primary > secondary > tertiary. Similar dehydrocoupling reactions using secondary amines with secondary silanes were found to be less reactive. Homodehydrocoupling of the silane was found not to be a competing reaction at room temperature. The hydride [(RNH)2UH][BPh4], which is plausibly formed in the reaction of [(RNH)3U][BPh4] with PhSiH3 is a likely intermediate in the catalytic cycle.

AB - Dehydrocoupling reactions of primary amines RNH2 with PhSiH3 were catalyzed by [(Et2N)3U][BPh4] to give the corresponding aminosilanes PhSiH3-n(NHR)n (n = 1-3), the relative yields of the products were found to be dependent on the experimental conditions and on the nature of R. For a primary silane (PhSiH3), the reactivity of RNH2 follows the order primary > secondary > tertiary. Similar dehydrocoupling reactions using secondary amines with secondary silanes were found to be less reactive. Homodehydrocoupling of the silane was found not to be a competing reaction at room temperature. The hydride [(RNH)2UH][BPh4], which is plausibly formed in the reaction of [(RNH)3U][BPh4] with PhSiH3 is a likely intermediate in the catalytic cycle.

KW - Amines

KW - Cationic

KW - Dehydrocoupling

KW - Silanes

KW - Uranium

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U2 - 10.1016/S0022-328X(00)00410-1

DO - 10.1016/S0022-328X(00)00410-1

M3 - 文章

AN - SCOPUS:0002205953

SN - 0022-328X

VL - 610

SP - 49

EP - 57

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

IS - 1-2

ER -

Dehydrocoupling reactions of amines with silanes catalyzed by [(Et₂N)₃U][BPh₄]

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