K2S2O8-Mediated Selective Trifluoromethylacylation and Trifluoromethylarylation of Alkenes under Transition-Metal-Free Conditions: Synthetic Scope and Mechanistic Studies
Lin Tang
1, 2
,
Zhen Yang
1
,
Xueping Chang
1
,
Jingchao Jiao
1
,
Xiantao Ma
1
,
Weihao Rao
1
,
Qiuju Zhou
1
,
Lingyun Zheng
1
2
Henan Province Key Laboratory of Utilization of Non-metallic Mineral in the Sourth of Henan, Xinyang, Henan 464000, China
|
Publication type: Journal Article
Publication date: 2018-10-05
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
30289263
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A practical and efficient method for selective intramolecular radical trifluoromethylacylation and -arylation of alkenes with inexpensive CF3SO2Na and K2S2O8 in aqueous media has been developed, respectively, affording the highly chemoselective synthesis of CF3-functionalized chroman-4-ones and chromanes in satisfactory yields. Control experiments and DFT calculations indicate that the CF3SO2Na/K2S2O8 system is capable of trifluoromethylating the substrate of alkenes without a transition metal catalyst and the oxidation of CF3SO2Na to ·CF3 by K2S2O8 is involved in the rate-determining step.
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87
Total citations:
87
Citations from 2025:
18
(20.69%)
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GOST
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Tang L. et al. K2S2O8-Mediated Selective Trifluoromethylacylation and Trifluoromethylarylation of Alkenes under Transition-Metal-Free Conditions: Synthetic Scope and Mechanistic Studies // Organic Letters. 2018. Vol. 20. No. 20. pp. 6520-6525.
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Tang L., Yang Z., Chang X., Jiao J., Ma X., Rao W., Zhou Q., Zheng L. K2S2O8-Mediated Selective Trifluoromethylacylation and Trifluoromethylarylation of Alkenes under Transition-Metal-Free Conditions: Synthetic Scope and Mechanistic Studies // Organic Letters. 2018. Vol. 20. No. 20. pp. 6520-6525.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.orglett.8b02846
UR - https://doi.org/10.1021/acs.orglett.8b02846
TI - K2S2O8-Mediated Selective Trifluoromethylacylation and Trifluoromethylarylation of Alkenes under Transition-Metal-Free Conditions: Synthetic Scope and Mechanistic Studies
T2 - Organic Letters
AU - Tang, Lin
AU - Yang, Zhen
AU - Chang, Xueping
AU - Jiao, Jingchao
AU - Ma, Xiantao
AU - Rao, Weihao
AU - Zhou, Qiuju
AU - Zheng, Lingyun
PY - 2018
DA - 2018/10/05
PB - American Chemical Society (ACS)
SP - 6520-6525
IS - 20
VL - 20
PMID - 30289263
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2018_Tang,
author = {Lin Tang and Zhen Yang and Xueping Chang and Jingchao Jiao and Xiantao Ma and Weihao Rao and Qiuju Zhou and Lingyun Zheng},
title = {K2S2O8-Mediated Selective Trifluoromethylacylation and Trifluoromethylarylation of Alkenes under Transition-Metal-Free Conditions: Synthetic Scope and Mechanistic Studies},
journal = {Organic Letters},
year = {2018},
volume = {20},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021/acs.orglett.8b02846},
number = {20},
pages = {6520--6525},
doi = {10.1021/acs.orglett.8b02846}
}
Cite this
MLA
Copy
Tang, Lin, et al. “K2S2O8-Mediated Selective Trifluoromethylacylation and Trifluoromethylarylation of Alkenes under Transition-Metal-Free Conditions: Synthetic Scope and Mechanistic Studies.” Organic Letters, vol. 20, no. 20, Oct. 2018, pp. 6520-6525. https://doi.org/10.1021/acs.orglett.8b02846.