Rhodium-Catalyzed Enamine Homologation of Sulfides with Triazoles as Carbene Precursor
Publication type: Journal Article
Publication date: 2020-08-13
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
32791000
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
We report on Rh(II)-catalyzed enamine homologation reactions of triazoles with cyclopropylmethyl sulfides. This reaction proceeds via Dimroth rearrangement of triazoles followed by rhodium-catalyzed ylide formation. This ylide, however, does not undergo classic rearrangement reactions. Instead, it undergoes a selective, intramolecular alkylation reaction to yield cyclopropylmethyl-substituted enamides. The application of this reaction was evaluated with different triazoles and sulfides, which underline the special reactivity of cyclopropylmethyl sulfides (29 examples, up to 83% yield).
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Total citations:
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Li F., Pei C., Koenigs R. M. Rhodium-Catalyzed Enamine Homologation of Sulfides with Triazoles as Carbene Precursor // Organic Letters. 2020. Vol. 22. No. 17. pp. 6816-6821.
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Li F., Pei C., Koenigs R. M. Rhodium-Catalyzed Enamine Homologation of Sulfides with Triazoles as Carbene Precursor // Organic Letters. 2020. Vol. 22. No. 17. pp. 6816-6821.
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RIS
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TY - JOUR
DO - 10.1021/acs.orglett.0c02330
UR - https://doi.org/10.1021/acs.orglett.0c02330
TI - Rhodium-Catalyzed Enamine Homologation of Sulfides with Triazoles as Carbene Precursor
T2 - Organic Letters
AU - Li, Fang
AU - Pei, Chao
AU - Koenigs, Rene M.
PY - 2020
DA - 2020/08/13
PB - American Chemical Society (ACS)
SP - 6816-6821
IS - 17
VL - 22
PMID - 32791000
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (up to 50 authors)
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@article{2020_Li,
author = {Fang Li and Chao Pei and Rene M. Koenigs},
title = {Rhodium-Catalyzed Enamine Homologation of Sulfides with Triazoles as Carbene Precursor},
journal = {Organic Letters},
year = {2020},
volume = {22},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021/acs.orglett.0c02330},
number = {17},
pages = {6816--6821},
doi = {10.1021/acs.orglett.0c02330}
}
Cite this
MLA
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Li, Fang, et al. “Rhodium-Catalyzed Enamine Homologation of Sulfides with Triazoles as Carbene Precursor.” Organic Letters, vol. 22, no. 17, Aug. 2020, pp. 6816-6821. https://doi.org/10.1021/acs.orglett.0c02330.