Open Access
ACS Omega, volume 7, issue 10, pages 9071-9079
Blue Light-Promoted Cross-Coupling of α-Diazo Esters with Isocyanides: Synthesis of Ester-Functionalized Ketenimines
Publication type: Journal Article
Publication date: 2022-03-03
PubMed ID:
35309460
General Chemistry
General Chemical Engineering
Abstract
A metal-free scalable synthesis of functionalized ketenimines from alkyl α-(aryl/heteroaryl)-α-diazoacetates and alkyl isocyanides induced by blue light irradiation has been developed. The reaction proceeds at room temperature without any photocatalyst and provides ketenimines in moderate to good yields. Density functional theory (DFT) calculations and the experimental study showed that aryl(alkoxycarbonyl)carbenes in both singlet and triplet states can react with isocyanides but only the reaction of the former leads to the smooth formation of ketenimines. The obtained ketenimines were used for the synthesis of functionalized amidines under mild metal-free conditions.
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Citations by publishers
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Sakharov P. A. et al. Blue Light-Promoted Cross-Coupling of α-Diazo Esters with Isocyanides: Synthesis of Ester-Functionalized Ketenimines // ACS Omega. 2022. Vol. 7. No. 10. pp. 9071-9079.
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Sakharov P. A., Novikov M. S., Nguyen T. K., Kinzhalov M. A., Khlebnikov A. F., Rostovskii N. V. Blue Light-Promoted Cross-Coupling of α-Diazo Esters with Isocyanides: Synthesis of Ester-Functionalized Ketenimines // ACS Omega. 2022. Vol. 7. No. 10. pp. 9071-9079.
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TY - JOUR
DO - 10.1021/acsomega.2c00367
UR - https://doi.org/10.1021%2Facsomega.2c00367
TI - Blue Light-Promoted Cross-Coupling of α-Diazo Esters with Isocyanides: Synthesis of Ester-Functionalized Ketenimines
T2 - ACS Omega
AU - Nguyen, Tuan K
AU - Sakharov, Pavel A
AU - Novikov, Mikhail S.
AU - Kinzhalov, M. A.
AU - Khlebnikov, Alexander F
AU - Rostovskii, Nikolai V
PY - 2022
DA - 2022/03/03 00:00:00
PB - American Chemical Society (ACS)
SP - 9071-9079
IS - 10
VL - 7
PMID - 35309460
SN - 2470-1343
ER -
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@article{2022_Sakharov,
author = {Tuan K Nguyen and Pavel A Sakharov and Mikhail S. Novikov and M. A. Kinzhalov and Alexander F Khlebnikov and Nikolai V Rostovskii},
title = {Blue Light-Promoted Cross-Coupling of α-Diazo Esters with Isocyanides: Synthesis of Ester-Functionalized Ketenimines},
journal = {ACS Omega},
year = {2022},
volume = {7},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021%2Facsomega.2c00367},
number = {10},
pages = {9071--9079},
doi = {10.1021/acsomega.2c00367}
}
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MLA
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Sakharov, Pavel A., et al. “Blue Light-Promoted Cross-Coupling of α-Diazo Esters with Isocyanides: Synthesis of Ester-Functionalized Ketenimines.” ACS Omega, vol. 7, no. 10, Mar. 2022, pp. 9071-9079. https://doi.org/10.1021%2Facsomega.2c00367.