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Chemical Science, volume 10, issue 4, pages 1201-1206
Gold-catalyzed (4+3)-annulations of 2-alkenyl-1-alkynylbenzenes with anthranils with alkyne-dependent chemoselectivity: skeletal rearrangement versus non-rearrangement
Publication type: Journal Article
Publication date: 2019-01-01
Journal:
Chemical Science
Q1
Q1
SJR: 2.333
CiteScore: 14.4
Impact factor: 7.6
ISSN: 20416520, 20416539
General Chemistry
Abstract
Two distinct (4+3)-nitroxy annulations between 1,5-enynes and anthranils have been developed to access tetrahydro-1H-benzo[b]azepine derivatives; the chemoselectivity varies with the types of alkynes. Terminal alkyne substrates deliver benzo[b]azepine derivatives via a novel skeletal rearrangement while internal 1,5-enynes afford products without a rearrangement process. To elucidate the mechanism of rearrangement, we performed 13C- and 2H-labeling experiments to identify the gold-containing isobenzofulvene intermediates, but their formation relies on the presence of anthranils.
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Singh R. R. et al. Gold-catalyzed (4+3)-annulations of 2-alkenyl-1-alkynylbenzenes with anthranils with alkyne-dependent chemoselectivity: skeletal rearrangement versus non-rearrangement // Chemical Science. 2019. Vol. 10. No. 4. pp. 1201-1206.
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Singh R. R., Skaria M., Chen L., Cheng M., Liu R. Gold-catalyzed (4+3)-annulations of 2-alkenyl-1-alkynylbenzenes with anthranils with alkyne-dependent chemoselectivity: skeletal rearrangement versus non-rearrangement // Chemical Science. 2019. Vol. 10. No. 4. pp. 1201-1206.
Cite this
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TY - JOUR
DO - 10.1039/c8sc03619e
UR - https://doi.org/10.1039/c8sc03619e
TI - Gold-catalyzed (4+3)-annulations of 2-alkenyl-1-alkynylbenzenes with anthranils with alkyne-dependent chemoselectivity: skeletal rearrangement versus non-rearrangement
T2 - Chemical Science
AU - Singh, Rahulkumar Rajmani
AU - Skaria, Manisha
AU - Chen, Lianzhu
AU - Cheng, Mu-Jeng
AU - Liu, Rai-Shung
PY - 2019
DA - 2019/01/01
PB - Royal Society of Chemistry (RSC)
SP - 1201-1206
IS - 4
VL - 10
SN - 2041-6520
SN - 2041-6539
ER -
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@article{2019_Singh,
author = {Rahulkumar Rajmani Singh and Manisha Skaria and Lianzhu Chen and Mu-Jeng Cheng and Rai-Shung Liu},
title = {Gold-catalyzed (4+3)-annulations of 2-alkenyl-1-alkynylbenzenes with anthranils with alkyne-dependent chemoselectivity: skeletal rearrangement versus non-rearrangement},
journal = {Chemical Science},
year = {2019},
volume = {10},
publisher = {Royal Society of Chemistry (RSC)},
month = {jan},
url = {https://doi.org/10.1039/c8sc03619e},
number = {4},
pages = {1201--1206},
doi = {10.1039/c8sc03619e}
}
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Singh, Rahulkumar Rajmani, et al. “Gold-catalyzed (4+3)-annulations of 2-alkenyl-1-alkynylbenzenes with anthranils with alkyne-dependent chemoselectivity: skeletal rearrangement versus non-rearrangement.” Chemical Science, vol. 10, no. 4, Jan. 2019, pp. 1201-1206. https://doi.org/10.1039/c8sc03619e.