Trimethylsilyl bis(trifluoromethanesulfonyl)imide as a tolerant and environmentally benign Lewis acid catalyst of the Diels–Alder reaction
2
European Institute of Chemistry and Biology (IECB-ENSCPB), 16 Avenue Pey-Berland, F-330607 Pessac, France
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Publication type: Journal Article
Publication date: 2002-10-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
N-trimethylsilyl bis(trifluoromethanesulfonyl)imide (TMSNTf2) was readily prepared in situ by protodesilylation of trimethylsilane, allyl- or phenyltrimethylsilane with bis(trifluoromethylsulfonyl)imide. NMR studies showed that TMSNTf2 was much more effective than TMSOTf in complexing the carbonyl group of trans-methylcrotonate. As a result, TMSNTf2 was found to be superior to TMSOTf as a catalyst for the Diels-Alder reaction of alpha,beta-unsaturated esters with a wide variety of dienes. In contrast to many metal derived Lewis acids, TMSNTf2 was found tolerant of many sensitive functional groups present in the diene partner. (C) 2002 Elsevier Science Ltd. All rights reserved.
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138
Total citations:
138
Citations from 2024:
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(2.89%)
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Mathieu B., Ghosez L. Trimethylsilyl bis(trifluoromethanesulfonyl)imide as a tolerant and environmentally benign Lewis acid catalyst of the Diels–Alder reaction // Tetrahedron. 2002. Vol. 58. No. 41. pp. 8219-8226.
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Mathieu B., Ghosez L. Trimethylsilyl bis(trifluoromethanesulfonyl)imide as a tolerant and environmentally benign Lewis acid catalyst of the Diels–Alder reaction // Tetrahedron. 2002. Vol. 58. No. 41. pp. 8219-8226.
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RIS
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TY - JOUR
DO - 10.1016/S0040-4020(02)00971-7
UR - https://doi.org/10.1016/S0040-4020(02)00971-7
TI - Trimethylsilyl bis(trifluoromethanesulfonyl)imide as a tolerant and environmentally benign Lewis acid catalyst of the Diels–Alder reaction
T2 - Tetrahedron
AU - Mathieu, Benoit
AU - Ghosez, L.
PY - 2002
DA - 2002/10/01
PB - Elsevier
SP - 8219-8226
IS - 41
VL - 58
SN - 0040-4020
SN - 1464-5416
ER -
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BibTex (up to 50 authors)
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@article{2002_Mathieu,
author = {Benoit Mathieu and L. Ghosez},
title = {Trimethylsilyl bis(trifluoromethanesulfonyl)imide as a tolerant and environmentally benign Lewis acid catalyst of the Diels–Alder reaction},
journal = {Tetrahedron},
year = {2002},
volume = {58},
publisher = {Elsevier},
month = {oct},
url = {https://doi.org/10.1016/S0040-4020(02)00971-7},
number = {41},
pages = {8219--8226},
doi = {10.1016/S0040-4020(02)00971-7}
}
Cite this
MLA
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Mathieu, Benoit, et al. “Trimethylsilyl bis(trifluoromethanesulfonyl)imide as a tolerant and environmentally benign Lewis acid catalyst of the Diels–Alder reaction.” Tetrahedron, vol. 58, no. 41, Oct. 2002, pp. 8219-8226. https://doi.org/10.1016/S0040-4020(02)00971-7.