Divergent Reactivity of Indole-Tethered Ynones with Silver(I) and Gold(I) Catalysts: A Combined Synthetic and Computational Study
Publication type: Journal Article
Publication date: 2018-07-04
scimago Q2
wos Q2
SJR: 0.559
CiteScore: 4.6
Impact factor: 2.3
ISSN: 00397881, 1437210X
Catalysis
Organic Chemistry
Abstract
A combined synthetic and computational (DFT) study has been performed to account for the divergent reactivity of indole-tethered ynones when treated with Ag(I) and Au(I) catalysts. The two catalyst systems deliver spirocyclic indolenines and carbazoles, respectively, from the same precursors, with the reaction outcomes believed to be a result of differences in the rates of a key protodemetalation step. A ring-opening/ring-closing isomerisation process is proposed to enable the interconversion of spirocyclic and C-2 annulated indole intermediates, in contrast to the 1,2-migration mechanism tentatively proposed in previous studies.
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24
Total citations:
24
Citations from 2024:
5
(20.83%)
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MLA
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GOST
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Lynam J. et al. Divergent Reactivity of Indole-Tethered Ynones with Silver(I) and Gold(I) Catalysts: A Combined Synthetic and Computational Study // Synthesis. 2018. Vol. 50. No. 24. pp. 4829-4836.
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Lynam J., Rossi Ashton J. A., Unsworth W., Lynam J. M., Taylor R., Unsworth W. P. Divergent Reactivity of Indole-Tethered Ynones with Silver(I) and Gold(I) Catalysts: A Combined Synthetic and Computational Study // Synthesis. 2018. Vol. 50. No. 24. pp. 4829-4836.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1055/s-0037-1610181
UR - https://doi.org/10.1055/s-0037-1610181
TI - Divergent Reactivity of Indole-Tethered Ynones with Silver(I) and Gold(I) Catalysts: A Combined Synthetic and Computational Study
T2 - Synthesis
AU - Lynam, Jason
AU - Rossi Ashton, James A
AU - Unsworth, William
AU - Lynam, Jason M.
AU - Taylor, R.
AU - Unsworth, William P.
PY - 2018
DA - 2018/07/04
PB - Georg Thieme Verlag KG
SP - 4829-4836
IS - 24
VL - 50
SN - 0039-7881
SN - 1437-210X
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2018_Lynam,
author = {Jason Lynam and James A Rossi Ashton and William Unsworth and Jason M. Lynam and R. Taylor and William P. Unsworth},
title = {Divergent Reactivity of Indole-Tethered Ynones with Silver(I) and Gold(I) Catalysts: A Combined Synthetic and Computational Study},
journal = {Synthesis},
year = {2018},
volume = {50},
publisher = {Georg Thieme Verlag KG},
month = {jul},
url = {https://doi.org/10.1055/s-0037-1610181},
number = {24},
pages = {4829--4836},
doi = {10.1055/s-0037-1610181}
}
Cite this
MLA
Copy
Lynam, Jason, et al. “Divergent Reactivity of Indole-Tethered Ynones with Silver(I) and Gold(I) Catalysts: A Combined Synthetic and Computational Study.” Synthesis, vol. 50, no. 24, Jul. 2018, pp. 4829-4836. https://doi.org/10.1055/s-0037-1610181.