CsF-Mediated in Situ Desilylation of TMS-Alkynes for Sonogashira Reaction
1
Vertex Pharmaceuticals Incorporated, 50 Northern Avenue, Boston, Massachusetts 02210, United States
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Publication type: Journal Article
Publication date: 2019-06-13
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
31194913
Organic Chemistry
Abstract
A practical and mild set of conditions for the Sonogashira reaction utilizing CsF-mediated in situ TMS-alkyne desilylation followed by Sonogashira coupling has been developed for the synthesis of a variety of alkynyl benzenes and heteroarenes in good to excellent yields. This methodology demonstrates excellent functional group tolerance and simple purification, which allows large-scale industrial applications. This one-pot protocol enables a high-yielding Sonogashira coupling with volatile alkynes by avoiding challenging isolation of free alkynes.
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Citations from 2025:
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(16.67%)
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GOST
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Capani J. S., Cochran J. E., Liang J. (. CsF-Mediated in Situ Desilylation of TMS-Alkynes for Sonogashira Reaction // Journal of Organic Chemistry. 2019. Vol. 84. No. 14. pp. 9378-9384.
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Capani J. S., Cochran J. E., Liang J. (. CsF-Mediated in Situ Desilylation of TMS-Alkynes for Sonogashira Reaction // Journal of Organic Chemistry. 2019. Vol. 84. No. 14. pp. 9378-9384.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.joc.9b01307
UR - https://doi.org/10.1021/acs.joc.9b01307
TI - CsF-Mediated in Situ Desilylation of TMS-Alkynes for Sonogashira Reaction
T2 - Journal of Organic Chemistry
AU - Capani, Joseph S
AU - Cochran, John E.
AU - Liang, Jianglin (colin)
PY - 2019
DA - 2019/06/13
PB - American Chemical Society (ACS)
SP - 9378-9384
IS - 14
VL - 84
PMID - 31194913
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2019_Capani,
author = {Joseph S Capani and John E. Cochran and Jianglin (colin) Liang},
title = {CsF-Mediated in Situ Desilylation of TMS-Alkynes for Sonogashira Reaction},
journal = {Journal of Organic Chemistry},
year = {2019},
volume = {84},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/acs.joc.9b01307},
number = {14},
pages = {9378--9384},
doi = {10.1021/acs.joc.9b01307}
}
Cite this
MLA
Copy
Capani, Joseph S., et al. “CsF-Mediated in Situ Desilylation of TMS-Alkynes for Sonogashira Reaction.” Journal of Organic Chemistry, vol. 84, no. 14, Jun. 2019, pp. 9378-9384. https://doi.org/10.1021/acs.joc.9b01307.