Catalytic Transformations of Alkynes into either α-Alkoxy or α-Aryl Enolates: Mannich Reactions by Cooperative Catalysis and Evidence for Nucleophile-Directed Chemoselectivity
Publication type: Journal Article
Publication date: 2018-10-08
scimago Q1
wos Q1
SJR: 5.550
CiteScore: 27.6
Impact factor: 16.9
ISSN: 14337851, 15213773
PubMed ID:
30047589
General Chemistry
Catalysis
Abstract
The catalytic formation of gold enolates from alkynes, nitrones, and nucleophiles is described, and their Mannich reactions result in nucleophile-directed chemoselectivity through cooperative catalysis. For 1-alkyn-4-ols and 2-ethynylphenols, their gold-catalyzed nitrone oxidations afforded N-containing dihydrofuran-3(2H)-ones with syn selectivity. The mechanism involves the Mannich reactions of gold enolates with imines through an O-H-N hydrogen-bonding motif. For aryloxyethynes, their gold enolates react selectively with nitrones to deliver 3-alkylidenebenzofuran-2-ones, as controlled by a C-H-O hydrogen-bonding motif.
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Metrics
58
Total citations:
58
Citations from 2024:
6
(10.35%)
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GOST
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Sahani R. L. et al. Catalytic Transformations of Alkynes into either α-Alkoxy or α-Aryl Enolates: Mannich Reactions by Cooperative Catalysis and Evidence for Nucleophile-Directed Chemoselectivity // Angewandte Chemie - International Edition. 2018. Vol. 57. No. 45. pp. 14878-14882.
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Sahani R. L., Patil M. D., Wagh S. B., Liu R. Catalytic Transformations of Alkynes into either α-Alkoxy or α-Aryl Enolates: Mannich Reactions by Cooperative Catalysis and Evidence for Nucleophile-Directed Chemoselectivity // Angewandte Chemie - International Edition. 2018. Vol. 57. No. 45. pp. 14878-14882.
Cite this
RIS
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TY - JOUR
DO - 10.1002/anie.201806883
UR - https://doi.org/10.1002/anie.201806883
TI - Catalytic Transformations of Alkynes into either α-Alkoxy or α-Aryl Enolates: Mannich Reactions by Cooperative Catalysis and Evidence for Nucleophile-Directed Chemoselectivity
T2 - Angewandte Chemie - International Edition
AU - Sahani, Rajkumar Lalji
AU - Patil, Manoj D
AU - Wagh, Sachin Bhausaheb
AU - Liu, Rai-Shung
PY - 2018
DA - 2018/10/08
PB - Wiley
SP - 14878-14882
IS - 45
VL - 57
PMID - 30047589
SN - 1433-7851
SN - 1521-3773
ER -
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@article{2018_Sahani,
author = {Rajkumar Lalji Sahani and Manoj D Patil and Sachin Bhausaheb Wagh and Rai-Shung Liu},
title = {Catalytic Transformations of Alkynes into either α-Alkoxy or α-Aryl Enolates: Mannich Reactions by Cooperative Catalysis and Evidence for Nucleophile-Directed Chemoselectivity},
journal = {Angewandte Chemie - International Edition},
year = {2018},
volume = {57},
publisher = {Wiley},
month = {oct},
url = {https://doi.org/10.1002/anie.201806883},
number = {45},
pages = {14878--14882},
doi = {10.1002/anie.201806883}
}
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MLA
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Sahani, Rajkumar Lalji, et al. “Catalytic Transformations of Alkynes into either α-Alkoxy or α-Aryl Enolates: Mannich Reactions by Cooperative Catalysis and Evidence for Nucleophile-Directed Chemoselectivity.” Angewandte Chemie - International Edition, vol. 57, no. 45, Oct. 2018, pp. 14878-14882. https://doi.org/10.1002/anie.201806883.