volume 10 issue 1 pages 148-152

Synthesis of N‐Heterocycles by Reductive Cyclization of Nitro Compounds using Formate Esters as Carbon Monoxide Surrogates

Publication typeJournal Article
Publication date2017-11-27
scimago Q1
wos Q2
SJR0.941
CiteScore6.1
Impact factor3.9
ISSN18673880, 18673899
Catalysis
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract

A series of alkyl and aryl formate esters were evaluated as CO sources in the Pd‐ and Pd/Ru‐catalyzed reductive cyclization of substituted nitro compounds to afford heterocycles, especially indoles. Phenyl formate was found to be the most effective, and it allowed the desired products to be obtained in excellent yields, often higher than those previously reported with pressurized CO. Through detailed experiments and kinetic studies, we were able to discern between metal‐catalyzed and base‐mediated activation of phenyl formate and confirmed that just the base was effective in catalyzing its decarbonylation.

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GOST |
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GOST Copy
Formenti D. et al. Synthesis of N‐Heterocycles by Reductive Cyclization of Nitro Compounds using Formate Esters as Carbon Monoxide Surrogates // ChemCatChem. 2017. Vol. 10. No. 1. pp. 148-152.
GOST all authors (up to 50) Copy
Formenti D., Ferretti F., Ragaini F. Synthesis of N‐Heterocycles by Reductive Cyclization of Nitro Compounds using Formate Esters as Carbon Monoxide Surrogates // ChemCatChem. 2017. Vol. 10. No. 1. pp. 148-152.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1002/cctc.201701214
UR - https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cctc.201701214
TI - Synthesis of N‐Heterocycles by Reductive Cyclization of Nitro Compounds using Formate Esters as Carbon Monoxide Surrogates
T2 - ChemCatChem
AU - Formenti, Dario
AU - Ferretti, Francesco
AU - Ragaini, Fabio
PY - 2017
DA - 2017/11/27
PB - Wiley
SP - 148-152
IS - 1
VL - 10
SN - 1867-3880
SN - 1867-3899
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2017_Formenti,
author = {Dario Formenti and Francesco Ferretti and Fabio Ragaini},
title = {Synthesis of N‐Heterocycles by Reductive Cyclization of Nitro Compounds using Formate Esters as Carbon Monoxide Surrogates},
journal = {ChemCatChem},
year = {2017},
volume = {10},
publisher = {Wiley},
month = {nov},
url = {https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cctc.201701214},
number = {1},
pages = {148--152},
doi = {10.1002/cctc.201701214}
}
MLA
Cite this
MLA Copy
Formenti, Dario, et al. “Synthesis of N‐Heterocycles by Reductive Cyclization of Nitro Compounds using Formate Esters as Carbon Monoxide Surrogates.” ChemCatChem, vol. 10, no. 1, Nov. 2017, pp. 148-152. https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cctc.201701214.