Photoredox Decarboxylative C(sp3)–N Coupling of α-Diazoacetates with Alkyl N-Hydroxyphthalimide Esters for Diversified Synthesis of Functionalized N-Alkyl Hydrazones
Тип публикации: Journal Article
Дата публикации: 2019-09-16
scimago Q1
wos Q1
БС1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
31524416
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Краткое описание
Herein we report a metal-free photocatalytic coupling reaction for the synthesis of structurally and functionally diverse N-alkyl hydrazones from α-diazoacetates and N-alkyl hydroxyphthalimide esters. By employing Rose Bengal as a photocatalyst with yellow LEDs irradiation, over 60 N-alkyl hydrazones were synthesized. Fluorescence quenching analysis and deuterium incorporation experiments reveal that Hantzsch ester serves as both an electron donor and proton source for the reaction. This strategy offers a simple retrosynthetic disconnection for conventionally inaccessible C(sp3)-rich N-alkyl hydrazones.
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Chan C. M. et al. Photoredox Decarboxylative C(sp3)–N Coupling of α-Diazoacetates with Alkyl N-Hydroxyphthalimide Esters for Diversified Synthesis of Functionalized N-Alkyl Hydrazones // Organic Letters. 2019. Vol. 21. No. 19. pp. 8037-8043.
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Chan C. M., Xing Q., Chow Y. C., Hung S. F., Yu W. X. Photoredox Decarboxylative C(sp3)–N Coupling of α-Diazoacetates with Alkyl N-Hydroxyphthalimide Esters for Diversified Synthesis of Functionalized N-Alkyl Hydrazones // Organic Letters. 2019. Vol. 21. No. 19. pp. 8037-8043.
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TY - JOUR
DO - 10.1021/acs.orglett.9b03020
UR - https://doi.org/10.1021/acs.orglett.9b03020
TI - Photoredox Decarboxylative C(sp3)–N Coupling of α-Diazoacetates with Alkyl N-Hydroxyphthalimide Esters for Diversified Synthesis of Functionalized N-Alkyl Hydrazones
T2 - Organic Letters
AU - Chan, Chun Ming
AU - Xing, Qi
AU - Chow, Yip Chi
AU - Hung, Sing Fung
AU - Yu, W. X.
PY - 2019
DA - 2019/09/16
PB - American Chemical Society (ACS)
SP - 8037-8043
IS - 19
VL - 21
PMID - 31524416
SN - 1523-7060
SN - 1523-7052
ER -
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@article{2019_Chan,
author = {Chun Ming Chan and Qi Xing and Yip Chi Chow and Sing Fung Hung and W. X. Yu},
title = {Photoredox Decarboxylative C(sp3)–N Coupling of α-Diazoacetates with Alkyl N-Hydroxyphthalimide Esters for Diversified Synthesis of Functionalized N-Alkyl Hydrazones},
journal = {Organic Letters},
year = {2019},
volume = {21},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://doi.org/10.1021/acs.orglett.9b03020},
number = {19},
pages = {8037--8043},
doi = {10.1021/acs.orglett.9b03020}
}
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MLA
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Chan, Chun Ming, et al. “Photoredox Decarboxylative C(sp3)–N Coupling of α-Diazoacetates with Alkyl N-Hydroxyphthalimide Esters for Diversified Synthesis of Functionalized N-Alkyl Hydrazones.” Organic Letters, vol. 21, no. 19, Sep. 2019, pp. 8037-8043. https://doi.org/10.1021/acs.orglett.9b03020.