Copper-Mediated Reactions of Nitriles with Nitromethanes: Aza-Henry Reactions and Nitrile Hydrations
Publication type: Journal Article
Publication date: 2018-02-07
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
29412678
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
In this study, the first aza-Henry reaction of nitriles with nitromethane in a CuI/Cs2CO3/DBU system is described. The process was conveniently and directly used for the synthesis of β-aminonitroalkenes 2a-x and tolerated aryl-, alkyl-, hetaryl-, alkenyl-, and alkynylnitriles. The resulting aminonitroalkenes 2 could be successfully transformed to the corresponding 2-nitroacetophenones, 2-amino-1-halonitroalkenes, 2-alkylaminonitroalkenes, or 3-nitropyridines. In the presence of H2O, the aza-Henry reaction turned the reaction path to the nitrile hydration to exclusively yield the amides 3a-s.
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15
Total citations:
15
Citations from 2024:
4
(26.66%)
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GOST
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Kuwabara J., Sawada Y., Yoshimatsu M. Copper-Mediated Reactions of Nitriles with Nitromethanes: Aza-Henry Reactions and Nitrile Hydrations // Organic Letters. 2018. Vol. 20. No. 4. pp. 1130-1133.
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Kuwabara J., Sawada Y., Yoshimatsu M. Copper-Mediated Reactions of Nitriles with Nitromethanes: Aza-Henry Reactions and Nitrile Hydrations // Organic Letters. 2018. Vol. 20. No. 4. pp. 1130-1133.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.orglett.8b00058
UR - https://doi.org/10.1021/acs.orglett.8b00058
TI - Copper-Mediated Reactions of Nitriles with Nitromethanes: Aza-Henry Reactions and Nitrile Hydrations
T2 - Organic Letters
AU - Kuwabara, Jun
AU - Sawada, Yoshiharu
AU - Yoshimatsu, Mitsuhiro
PY - 2018
DA - 2018/02/07
PB - American Chemical Society (ACS)
SP - 1130-1133
IS - 4
VL - 20
PMID - 29412678
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
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@article{2018_Kuwabara,
author = {Jun Kuwabara and Yoshiharu Sawada and Mitsuhiro Yoshimatsu},
title = {Copper-Mediated Reactions of Nitriles with Nitromethanes: Aza-Henry Reactions and Nitrile Hydrations},
journal = {Organic Letters},
year = {2018},
volume = {20},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://doi.org/10.1021/acs.orglett.8b00058},
number = {4},
pages = {1130--1133},
doi = {10.1021/acs.orglett.8b00058}
}
Cite this
MLA
Copy
Kuwabara, Jun, et al. “Copper-Mediated Reactions of Nitriles with Nitromethanes: Aza-Henry Reactions and Nitrile Hydrations.” Organic Letters, vol. 20, no. 4, Feb. 2018, pp. 1130-1133. https://doi.org/10.1021/acs.orglett.8b00058.