volume 25 issue 31 pages 5890-5895

Rhodium-Catalyzed Selective Nucleophilic Cyclization/Cross-Coupling of Two ortho-Alkynylanilines Bearing Differential N-Substituents

Jin-chen Li 1
Jiale Li 1
Bing Xia Yan 1
Bing-Xia Yan 1
Gang Wang 1
Zhi Shi Ye 1
Publication typeJournal Article
Publication date2023-08-02
scimago Q1
wos Q1
SJR1.235
CiteScore8.7
Impact factor5.0
ISSN15237060, 15237052
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
Herein, we reported an effective selective nucleophilic cyclization/cross-coupling cascade reaction of N-tosyl ortho-alkynylanilines and N-acyl ortho-alkynylanilines using Rh(COD)2BF4/tBuXantPhos as a catalyst. The present protocol features excellent chemo- and regioselectivity, high atom-economy, and a broad range of substrates. The mechanism studies indicated that the key to the success of this reaction is the powerful capacity of the rhodium catalyst to recognize the N-substituent group in the selective nucleophilic cyclization and selective alkyne insertion.
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GOST Copy
Li J. et al. Rhodium-Catalyzed Selective Nucleophilic Cyclization/Cross-Coupling of Two ortho-Alkynylanilines Bearing Differential N-Substituents // Organic Letters. 2023. Vol. 25. No. 31. pp. 5890-5895.
GOST all authors (up to 50) Copy
Li J., Li J., Yan B. X., Yan B., Wang G., Ye Z. S. Rhodium-Catalyzed Selective Nucleophilic Cyclization/Cross-Coupling of Two ortho-Alkynylanilines Bearing Differential N-Substituents // Organic Letters. 2023. Vol. 25. No. 31. pp. 5890-5895.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1021/acs.orglett.3c02180
UR - https://pubs.acs.org/doi/10.1021/acs.orglett.3c02180
TI - Rhodium-Catalyzed Selective Nucleophilic Cyclization/Cross-Coupling of Two ortho-Alkynylanilines Bearing Differential N-Substituents
T2 - Organic Letters
AU - Li, Jin-chen
AU - Li, Jiale
AU - Yan, Bing Xia
AU - Yan, Bing-Xia
AU - Wang, Gang
AU - Ye, Zhi Shi
PY - 2023
DA - 2023/08/02
PB - American Chemical Society (ACS)
SP - 5890-5895
IS - 31
VL - 25
PMID - 37530173
SN - 1523-7060
SN - 1523-7052
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2023_Li,
author = {Jin-chen Li and Jiale Li and Bing Xia Yan and Bing-Xia Yan and Gang Wang and Zhi Shi Ye},
title = {Rhodium-Catalyzed Selective Nucleophilic Cyclization/Cross-Coupling of Two ortho-Alkynylanilines Bearing Differential N-Substituents},
journal = {Organic Letters},
year = {2023},
volume = {25},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://pubs.acs.org/doi/10.1021/acs.orglett.3c02180},
number = {31},
pages = {5890--5895},
doi = {10.1021/acs.orglett.3c02180}
}
MLA
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MLA Copy
Li, Jin-chen, et al. “Rhodium-Catalyzed Selective Nucleophilic Cyclization/Cross-Coupling of Two ortho-Alkynylanilines Bearing Differential N-Substituents.” Organic Letters, vol. 25, no. 31, Aug. 2023, pp. 5890-5895. https://pubs.acs.org/doi/10.1021/acs.orglett.3c02180.