Collective Synthesis of 3-Acylindoles, Indole-3-carboxylic Esters, Indole-3-sulfinic Acids, and 3-(Methylsulfonyl)indoles from Free (N–H) Indoles via Common N-Indolyl Triethylborate
Zhi Wei Zhang
1
,
Hong Xue
1
,
Hailing Li
1
,
Huaiping Kang
1
,
Juan Feng
1
,
Aijun Lin
2
,
Shouxin Liu
1
Publication type: Journal Article
Publication date: 2016-07-26
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
27457258
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A general and direct C3 functionalization of free (N-H) indoles with readily available electrophiles such as acid chlorides, chloroformates, thionyl chloride, and methylsulfonyl chloride via a common N-indolyl triethylborate intermediate is reported. The reaction proceeds smoothly under mild conditions in up to 93% yield. Indoles with substituents at the C2, C4, C5, C6, and C7 positions are well tolerated. The easy accessibility of a variety of important 3-acylindoles, indole-3-carboxylic esters, indole-3-sulfinic acids, and 3-(methylsulfonyl)indoles demonstrates the high degree of compatibility and practicability of this method.
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32
Total citations:
32
Citations from 2024:
10
(31%)
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GOST
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Zhang Z. W. et al. Collective Synthesis of 3-Acylindoles, Indole-3-carboxylic Esters, Indole-3-sulfinic Acids, and 3-(Methylsulfonyl)indoles from Free (N–H) Indoles via Common N-Indolyl Triethylborate // Organic Letters. 2016. Vol. 18. No. 15. pp. 3918-3921.
GOST all authors (up to 50)
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Zhang Z. W., Xue H., Li H., Kang H., Feng J., Lin A., Liu S. Collective Synthesis of 3-Acylindoles, Indole-3-carboxylic Esters, Indole-3-sulfinic Acids, and 3-(Methylsulfonyl)indoles from Free (N–H) Indoles via Common N-Indolyl Triethylborate // Organic Letters. 2016. Vol. 18. No. 15. pp. 3918-3921.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.orglett.6b01970
UR - https://doi.org/10.1021/acs.orglett.6b01970
TI - Collective Synthesis of 3-Acylindoles, Indole-3-carboxylic Esters, Indole-3-sulfinic Acids, and 3-(Methylsulfonyl)indoles from Free (N–H) Indoles via Common N-Indolyl Triethylborate
T2 - Organic Letters
AU - Zhang, Zhi Wei
AU - Xue, Hong
AU - Li, Hailing
AU - Kang, Huaiping
AU - Feng, Juan
AU - Lin, Aijun
AU - Liu, Shouxin
PY - 2016
DA - 2016/07/26
PB - American Chemical Society (ACS)
SP - 3918-3921
IS - 15
VL - 18
PMID - 27457258
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2016_Zhang,
author = {Zhi Wei Zhang and Hong Xue and Hailing Li and Huaiping Kang and Juan Feng and Aijun Lin and Shouxin Liu},
title = {Collective Synthesis of 3-Acylindoles, Indole-3-carboxylic Esters, Indole-3-sulfinic Acids, and 3-(Methylsulfonyl)indoles from Free (N–H) Indoles via Common N-Indolyl Triethylborate},
journal = {Organic Letters},
year = {2016},
volume = {18},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://doi.org/10.1021/acs.orglett.6b01970},
number = {15},
pages = {3918--3921},
doi = {10.1021/acs.orglett.6b01970}
}
Cite this
MLA
Copy
Zhang, Zhi Wei, et al. “Collective Synthesis of 3-Acylindoles, Indole-3-carboxylic Esters, Indole-3-sulfinic Acids, and 3-(Methylsulfonyl)indoles from Free (N–H) Indoles via Common N-Indolyl Triethylborate.” Organic Letters, vol. 18, no. 15, Jul. 2016, pp. 3918-3921. https://doi.org/10.1021/acs.orglett.6b01970.