Divergent oriented synthesis (DOS) of aza-heterocyclic amides through palladium-catalyzed ketenimination of 2-iodo-N-(propa-1,2-dien-1-yl)anilines
Xiaoyan Chen
1, 2, 3, 4, 5, 6
,
Guanyinsheng Qiu
7, 8, 9, 10, 11, 12
,
Renzhi Liu
7, 8, 9, 10, 11, 12
,
Dianpeng Chen
12, 13, 14, 15, 16
,
Zhiyuan Chen
1, 2, 3, 4, 5, 6
2
Key Laboratory of Functional Small Organic Molecules
3
Ministry of Education and College of Chemistry & Chemical Engineering
4
JiangXi Normal University
|
5
Nanchang
|
6
P. R. China
|
8
College of Biological
9
Chemical Sciences and Engineering
11
Jiaxing 314001
|
12
CHINA
|
14
Chemistry and Chemical Engineering
16
Qufu 273165
|
Publication type: Journal Article
Publication date: 2020-02-21
scimago Q1
wos Q1
SJR: 1.068
CiteScore: 8.2
Impact factor: 4.7
ISSN: 20524110, 20524129
Organic Chemistry
Abstract
A palladium-catalyzed tandem reaction of N-(2-iodophenyl)-4-methyl-N-(propa-1,2-dien-1-yl)benzenesulfonamide with isocyanide is described to divergently produce aza-heterocyclic amides. The success of this reaction relies on a versatile synthetic intermediate, 2-(1H-indol-3-yl)ethen-1-imine, which was proposed to be generated through oxidative addition of palladium, regioselective addition of an allene group, 1,1-insertion of isocyanides, and β-H elimination.
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38
Total citations:
38
Citations from 2025:
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(7.89%)
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Chen X. et al. Divergent oriented synthesis (DOS) of aza-heterocyclic amides through palladium-catalyzed ketenimination of 2-iodo-N-(propa-1,2-dien-1-yl)anilines // Organic Chemistry Frontiers. 2020. Vol. 7. No. 6. pp. 890-895.
GOST all authors (up to 50)
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Chen X., Qiu G., Liu R., Chen D., Chen Z. Divergent oriented synthesis (DOS) of aza-heterocyclic amides through palladium-catalyzed ketenimination of 2-iodo-N-(propa-1,2-dien-1-yl)anilines // Organic Chemistry Frontiers. 2020. Vol. 7. No. 6. pp. 890-895.
Cite this
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TY - JOUR
DO - 10.1039/C9QO01451A
UR - https://xlink.rsc.org/?DOI=C9QO01451A
TI - Divergent oriented synthesis (DOS) of aza-heterocyclic amides through palladium-catalyzed ketenimination of 2-iodo-N-(propa-1,2-dien-1-yl)anilines
T2 - Organic Chemistry Frontiers
AU - Chen, Xiaoyan
AU - Qiu, Guanyinsheng
AU - Liu, Renzhi
AU - Chen, Dianpeng
AU - Chen, Zhiyuan
PY - 2020
DA - 2020/02/21
PB - Royal Society of Chemistry (RSC)
SP - 890-895
IS - 6
VL - 7
SN - 2052-4110
SN - 2052-4129
ER -
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@article{2020_Chen,
author = {Xiaoyan Chen and Guanyinsheng Qiu and Renzhi Liu and Dianpeng Chen and Zhiyuan Chen},
title = {Divergent oriented synthesis (DOS) of aza-heterocyclic amides through palladium-catalyzed ketenimination of 2-iodo-N-(propa-1,2-dien-1-yl)anilines},
journal = {Organic Chemistry Frontiers},
year = {2020},
volume = {7},
publisher = {Royal Society of Chemistry (RSC)},
month = {feb},
url = {https://xlink.rsc.org/?DOI=C9QO01451A},
number = {6},
pages = {890--895},
doi = {10.1039/C9QO01451A}
}
Cite this
MLA
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Chen, Xiaoyan, et al. “Divergent oriented synthesis (DOS) of aza-heterocyclic amides through palladium-catalyzed ketenimination of 2-iodo-N-(propa-1,2-dien-1-yl)anilines.” Organic Chemistry Frontiers, vol. 7, no. 6, Feb. 2020, pp. 890-895. https://xlink.rsc.org/?DOI=C9QO01451A.