Brønsted-Acid-Promoted Rh-Catalyzed Asymmetric Hydrogenation of N-Unprotected Indoles: A Cocatalysis of Transition Metal and Anion Binding
Jialin Wen
1, 2
,
Xiangru Fan
1
,
Renchang Tan
3
,
Hui-Chun Chien
3
,
Qinghai Zhou
1
,
Lung Wa Chung
1
,
Xumu Zhang
1
Publication type: Journal Article
Publication date: 2018-03-30
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
29600702
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
The incorporation of Brønsted acid, thiourea anion binding, and transition metal catalysis enables an efficient method to synthesize chiral indolines via hydrogenation of indoles. Catalyzed by a rhodium/ZhaoPhos complex, asymmetric hydrogenation of unprotected indoles is performed smoothly with excellent enantioselectivities (up to 99% ee, up to 400 TON). Brønsted acid HCl activates indoles to form iminium ion intermediates. Mechanistic studies support the assumption that anion binding plays a crucial role as a secondary interaction. DFT calculations reveal an outer-sphere mechanism in this chemical transformation.
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75
Total citations:
75
Citations from 2024:
14
(18.66%)
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GOST
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Wen J. et al. Brønsted-Acid-Promoted Rh-Catalyzed Asymmetric Hydrogenation of N-Unprotected Indoles: A Cocatalysis of Transition Metal and Anion Binding // Organic Letters. 2018. Vol. 20. No. 8. pp. 2143-2147.
GOST all authors (up to 50)
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Wen J., Fan X., Tan R., Chien H., Zhou Q., Chung L. W., Zhang X. Brønsted-Acid-Promoted Rh-Catalyzed Asymmetric Hydrogenation of N-Unprotected Indoles: A Cocatalysis of Transition Metal and Anion Binding // Organic Letters. 2018. Vol. 20. No. 8. pp. 2143-2147.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.orglett.8b00312
UR - https://doi.org/10.1021/acs.orglett.8b00312
TI - Brønsted-Acid-Promoted Rh-Catalyzed Asymmetric Hydrogenation of N-Unprotected Indoles: A Cocatalysis of Transition Metal and Anion Binding
T2 - Organic Letters
AU - Wen, Jialin
AU - Fan, Xiangru
AU - Tan, Renchang
AU - Chien, Hui-Chun
AU - Zhou, Qinghai
AU - Chung, Lung Wa
AU - Zhang, Xumu
PY - 2018
DA - 2018/03/30
PB - American Chemical Society (ACS)
SP - 2143-2147
IS - 8
VL - 20
PMID - 29600702
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
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@article{2018_Wen,
author = {Jialin Wen and Xiangru Fan and Renchang Tan and Hui-Chun Chien and Qinghai Zhou and Lung Wa Chung and Xumu Zhang},
title = {Brønsted-Acid-Promoted Rh-Catalyzed Asymmetric Hydrogenation of N-Unprotected Indoles: A Cocatalysis of Transition Metal and Anion Binding},
journal = {Organic Letters},
year = {2018},
volume = {20},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/acs.orglett.8b00312},
number = {8},
pages = {2143--2147},
doi = {10.1021/acs.orglett.8b00312}
}
Cite this
MLA
Copy
Wen, Jialin, et al. “Brønsted-Acid-Promoted Rh-Catalyzed Asymmetric Hydrogenation of N-Unprotected Indoles: A Cocatalysis of Transition Metal and Anion Binding.” Organic Letters, vol. 20, no. 8, Mar. 2018, pp. 2143-2147. https://doi.org/10.1021/acs.orglett.8b00312.