Rhodium(III)‐Catalyzed Atroposelective Synthesis of Biaryls by C−H Activation and Intermolecular Coupling with Sterically Hindered Alkynes
Тип публикации: Journal Article
Дата публикации: 2020-05-26
scimago Q1
wos Q1
БС1
SJR: 5.550
CiteScore: 27.6
Impact factor: 16.9
ISSN: 14337851, 15213773
PubMed ID:
32298051
General Chemistry
Catalysis
Краткое описание
Reported herein is the atroposelective synthesis of biaryl NH isoquinolones by RhIII -catalyzed C-H activation of benzamides and intermolecular [4+2] annulation for a broad scope of 2-substituted 1-alkynylnaphthalenes, as well as sterically hindered, symmetric diarylacetylenes. The axial chirality is constructed based on dynamic kinetic transformation of the alkyne in redox-neutral annulation with benzamides, with alkyne insertion being stereodetermining. The reaction accommodates both benzamides and heteroaryl carboxamides and proceeds in excellent regioselectivity (if applicable) and enantioselectivities (average 91.8 % ee). An enantiomerically and diastereomerically pure rhodacyclic complex was prepared and offers insight into enantiomeric control of the coupling system, wherein the steric interactions between the amide directing group and the alkyne substrate dictate both the regio- and enantioselectivity.
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Wang F. et al. Rhodium(III)‐Catalyzed Atroposelective Synthesis of Biaryls by C−H Activation and Intermolecular Coupling with Sterically Hindered Alkynes // Angewandte Chemie - International Edition. 2020. Vol. 59. No. 32. pp. 13288-13294.
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Wang F., Qi Z., ZHAO Y., Zhai S., Zheng G., Mi R., Huang Z., Zhu X., He X., Li X. Rhodium(III)‐Catalyzed Atroposelective Synthesis of Biaryls by C−H Activation and Intermolecular Coupling with Sterically Hindered Alkynes // Angewandte Chemie - International Edition. 2020. Vol. 59. No. 32. pp. 13288-13294.
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TY - JOUR
DO - 10.1002/anie.202002208
UR - https://doi.org/10.1002/anie.202002208
TI - Rhodium(III)‐Catalyzed Atroposelective Synthesis of Biaryls by C−H Activation and Intermolecular Coupling with Sterically Hindered Alkynes
T2 - Angewandte Chemie - International Edition
AU - Wang, Fen
AU - Qi, Zisong
AU - ZHAO, YUXIA
AU - Zhai, Shuailei
AU - Zheng, Guangfan
AU - Mi, Ruijie
AU - Huang, Zhiyan
AU - Zhu, Xiaolin
AU - He, Xiaoming
AU - Li, Xingwei
PY - 2020
DA - 2020/05/26
PB - Wiley
SP - 13288-13294
IS - 32
VL - 59
PMID - 32298051
SN - 1433-7851
SN - 1521-3773
ER -
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@article{2020_Wang,
author = {Fen Wang and Zisong Qi and YUXIA ZHAO and Shuailei Zhai and Guangfan Zheng and Ruijie Mi and Zhiyan Huang and Xiaolin Zhu and Xiaoming He and Xingwei Li},
title = {Rhodium(III)‐Catalyzed Atroposelective Synthesis of Biaryls by C−H Activation and Intermolecular Coupling with Sterically Hindered Alkynes},
journal = {Angewandte Chemie - International Edition},
year = {2020},
volume = {59},
publisher = {Wiley},
month = {may},
url = {https://doi.org/10.1002/anie.202002208},
number = {32},
pages = {13288--13294},
doi = {10.1002/anie.202002208}
}
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MLA
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Wang, Fen, et al. “Rhodium(III)‐Catalyzed Atroposelective Synthesis of Biaryls by C−H Activation and Intermolecular Coupling with Sterically Hindered Alkynes.” Angewandte Chemie - International Edition, vol. 59, no. 32, May. 2020, pp. 13288-13294. https://doi.org/10.1002/anie.202002208.