Broad Survey of Selectivity in the Heterogeneous Hydrogenation of Heterocycles
Thomas W Lyons
1
,
Isabelle Nathalie Marie Leibler
2
,
Cyndi Qixin He
3
,
Surendra Gadamsetty
4
,
Gregorio J. Estrada
2
,
Abigail G. Doyle
2
1
Department of Process Research and Development, Merck & Co., Inc., Boston, Massachusetts 02115, United States
|
3
Modeling & Informatics, Merck & Co., Inc., Rahway, New Jersey 07065, United States
|
4
Department of Process Research and Development, Merck & Co., Inc., Rahway, New Jersey 07065, United States
|
Publication type: Journal Article
Publication date: 2024-01-19
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
38241605
Organic Chemistry
Abstract
A broad survey of heterogeneous hydrogenation catalysts has been conducted for the reduction of heterocycles commonly found in pharmaceuticals. The comparative reactivity of these substrates is reported as a function of catalyst, temperature, and hydrogen pressure. This analysis provided several catalysts with complementary reactivity between substrates. We then explored a series of bisheterocyclic substrates that provided an intramolecular competition of heterocycle hydrogenation reactivity. In several cases, complete selectivity could be achieved for reduction of one heterocycle and isolated yields are reported. A general trend in reactivity is inferred in which quinoline is the most reactive, followed by pyrazine, then pyrrole and with pyridine being the least reactive.
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13
Total citations:
13
Citations from 2024:
13
(100%)
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GOST
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Lyons T. W. et al. Broad Survey of Selectivity in the Heterogeneous Hydrogenation of Heterocycles // Journal of Organic Chemistry. 2024. Vol. 89. No. 3. pp. 1438-1445.
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Lyons T. W., Leibler I. N. M., He C. Q., Gadamsetty S., Estrada G. J., Doyle A. G. Broad Survey of Selectivity in the Heterogeneous Hydrogenation of Heterocycles // Journal of Organic Chemistry. 2024. Vol. 89. No. 3. pp. 1438-1445.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.joc.3c02028
UR - https://pubs.acs.org/doi/10.1021/acs.joc.3c02028
TI - Broad Survey of Selectivity in the Heterogeneous Hydrogenation of Heterocycles
T2 - Journal of Organic Chemistry
AU - Lyons, Thomas W
AU - Leibler, Isabelle Nathalie Marie
AU - He, Cyndi Qixin
AU - Gadamsetty, Surendra
AU - Estrada, Gregorio J.
AU - Doyle, Abigail G.
PY - 2024
DA - 2024/01/19
PB - American Chemical Society (ACS)
SP - 1438-1445
IS - 3
VL - 89
PMID - 38241605
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2024_Lyons,
author = {Thomas W Lyons and Isabelle Nathalie Marie Leibler and Cyndi Qixin He and Surendra Gadamsetty and Gregorio J. Estrada and Abigail G. Doyle},
title = {Broad Survey of Selectivity in the Heterogeneous Hydrogenation of Heterocycles},
journal = {Journal of Organic Chemistry},
year = {2024},
volume = {89},
publisher = {American Chemical Society (ACS)},
month = {jan},
url = {https://pubs.acs.org/doi/10.1021/acs.joc.3c02028},
number = {3},
pages = {1438--1445},
doi = {10.1021/acs.joc.3c02028}
}
Cite this
MLA
Copy
Lyons, Thomas W., et al. “Broad Survey of Selectivity in the Heterogeneous Hydrogenation of Heterocycles.” Journal of Organic Chemistry, vol. 89, no. 3, Jan. 2024, pp. 1438-1445. https://pubs.acs.org/doi/10.1021/acs.joc.3c02028.