Copper(ii)-catalyzed Chan-Lam cross-coupling: chemoselective N-arylation of aminophenols.
A Siva Reddy
1, 2
,
K Ranjith Reddy
1, 2
,
D Nageswar Rao
1, 2
,
Chaitanya K Jaladanki
3
,
Patrick Y S Lam
4
,
Parthasarathi Das
1, 2
1
2
Academy of Scientific and Innovative Research (AcSIR), New Delhi-110025, India
|
3
Department of Medicinal Chemistry, National Institute of Educational and Research (NIPER), S.A.S Nagar, Mohali, Punjab-160062, India
|
4
Baruch S. Blumberg Institute, 3805 Old Easton Road, Doylestown, PA 18902, USA
|
Publication type: Journal Article
Publication date: 2017-01-01
scimago Q2
wos Q2
SJR: 0.600
CiteScore: 5.2
Impact factor: 2.7
ISSN: 14770520, 14770539
PubMed ID:
28045171
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
Copper(ii)-catalyzed boronic acid promoted chemoselective N-arylation of unprotected aminophenols has been developed. Selective N-arylation of 3-aminophenol is achieved with a Cu(OAc)2/AgOAc combination in MeOH at rt, whereas the chemoselective N-arylated products of 4-aminophenol can be obtained with a Cu(OAc)2/Cs2CO3 system and benzoic acid as an additive. These ligand-free conditions and "open-flask" chemistry are robust and compatible with a wide range of functional groups. The mechanistic investigation for this selective N-arylation has been studied by considering Density Functional Theory (DFT) calculations.
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55
Total citations:
55
Citations from 2024:
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(12.73%)
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GOST
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Siva Reddy A. et al. Copper(ii)-catalyzed Chan-Lam cross-coupling: chemoselective N-arylation of aminophenols. // Organic and Biomolecular Chemistry. 2017. Vol. 15. No. 4. pp. 801-806.
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Siva Reddy A., Ranjith Reddy K., Nageswar Rao D., Jaladanki C. K., Bharatam P. V., Lam P. Y. S., Das P. Copper(ii)-catalyzed Chan-Lam cross-coupling: chemoselective N-arylation of aminophenols. // Organic and Biomolecular Chemistry. 2017. Vol. 15. No. 4. pp. 801-806.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1039/C6OB02444K
UR - https://doi.org/10.1039/C6OB02444K
TI - Copper(ii)-catalyzed Chan-Lam cross-coupling: chemoselective N-arylation of aminophenols.
T2 - Organic and Biomolecular Chemistry
AU - Siva Reddy, A
AU - Ranjith Reddy, K
AU - Nageswar Rao, D
AU - Jaladanki, Chaitanya K
AU - Bharatam, Prasad V.
AU - Lam, Patrick Y S
AU - Das, Parthasarathi
PY - 2017
DA - 2017/01/01
PB - Royal Society of Chemistry (RSC)
SP - 801-806
IS - 4
VL - 15
PMID - 28045171
SN - 1477-0520
SN - 1477-0539
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2017_Siva Reddy,
author = {A Siva Reddy and K Ranjith Reddy and D Nageswar Rao and Chaitanya K Jaladanki and Prasad V. Bharatam and Patrick Y S Lam and Parthasarathi Das},
title = {Copper(ii)-catalyzed Chan-Lam cross-coupling: chemoselective N-arylation of aminophenols.},
journal = {Organic and Biomolecular Chemistry},
year = {2017},
volume = {15},
publisher = {Royal Society of Chemistry (RSC)},
month = {jan},
url = {https://doi.org/10.1039/C6OB02444K},
number = {4},
pages = {801--806},
doi = {10.1039/C6OB02444K}
}
Cite this
MLA
Copy
Siva Reddy, A., et al. “Copper(ii)-catalyzed Chan-Lam cross-coupling: chemoselective N-arylation of aminophenols..” Organic and Biomolecular Chemistry, vol. 15, no. 4, Jan. 2017, pp. 801-806. https://doi.org/10.1039/C6OB02444K.
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