volume 25 issue 23 pages 4298-4302

Synthesis of 2-Formyl Carbazoles via Tandem Reaction of Indolyl Nitrones with 2-Methylidene Cyclic Carbonate

Sujin Min 1
Taeeun Kim 1
T.-e. Kim 1
Taejoo Jeong 1
Junhyeok Yang 1
Yebin Oh 1
Kyeongwon Moon 1
Amitava Rakshit 1
Publication typeJournal Article
Publication date2023-06-07
scimago Q1
wos Q1
SJR1.235
CiteScore8.7
Impact factor5.0
ISSN15237060, 15237052
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
The synthesis of functionalized carbazoles as privileged nitrogen heterocycles has emerged as a central topic in drug discovery and material science. We herein disclose the rhodium(III)-catalyzed cross-coupling reaction between indolyl nitrones and 2-methylidene cyclic carbonate as an allylating surrogate, resulting in the formation of C2-formylated carbazoles via tandem C–H allylation, [3 + 2] cycloaddition, aromatization, and benzylic oxidation. The synthetic utility of this protocol is highlighted by a variety of post-transformations of C2-formylated carbazoles.
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GOST Copy
Min S. et al. Synthesis of 2-Formyl Carbazoles via Tandem Reaction of Indolyl Nitrones with 2-Methylidene Cyclic Carbonate // Organic Letters. 2023. Vol. 25. No. 23. pp. 4298-4302.
GOST all authors (up to 50) Copy
Min S., Kim T., Kim T., Jeong T., Yang J., Oh Y., Moon K., Rakshit A., Kim I. S. Synthesis of 2-Formyl Carbazoles via Tandem Reaction of Indolyl Nitrones with 2-Methylidene Cyclic Carbonate // Organic Letters. 2023. Vol. 25. No. 23. pp. 4298-4302.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1021/acs.orglett.3c01336
UR - https://pubs.acs.org/doi/10.1021/acs.orglett.3c01336
TI - Synthesis of 2-Formyl Carbazoles via Tandem Reaction of Indolyl Nitrones with 2-Methylidene Cyclic Carbonate
T2 - Organic Letters
AU - Min, Sujin
AU - Kim, Taeeun
AU - Kim, T.-e.
AU - Jeong, Taejoo
AU - Yang, Junhyeok
AU - Oh, Yebin
AU - Moon, Kyeongwon
AU - Rakshit, Amitava
AU - Kim, In Su
PY - 2023
DA - 2023/06/07
PB - American Chemical Society (ACS)
SP - 4298-4302
IS - 23
VL - 25
PMID - 37283370
SN - 1523-7060
SN - 1523-7052
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2023_Min,
author = {Sujin Min and Taeeun Kim and T.-e. Kim and Taejoo Jeong and Junhyeok Yang and Yebin Oh and Kyeongwon Moon and Amitava Rakshit and In Su Kim},
title = {Synthesis of 2-Formyl Carbazoles via Tandem Reaction of Indolyl Nitrones with 2-Methylidene Cyclic Carbonate},
journal = {Organic Letters},
year = {2023},
volume = {25},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://pubs.acs.org/doi/10.1021/acs.orglett.3c01336},
number = {23},
pages = {4298--4302},
doi = {10.1021/acs.orglett.3c01336}
}
MLA
Cite this
MLA Copy
Min, Sujin, et al. “Synthesis of 2-Formyl Carbazoles via Tandem Reaction of Indolyl Nitrones with 2-Methylidene Cyclic Carbonate.” Organic Letters, vol. 25, no. 23, Jun. 2023, pp. 4298-4302. https://pubs.acs.org/doi/10.1021/acs.orglett.3c01336.
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