A Thermo-regulated Highly Regioselective Mono and Dihalogenations of Phenols and Anilines in Water Employing New Lewis Base Adducts (LBAs) [DBUBr]+Br- and [DBUI]+I- As Green Reagents; A Simple Approach
Vijayalaxmi Gavinolla
1
,
Swathi Thangalipalli
1
,
Siddarama Goud Bandalla
2
,
Panduga Ramaraju
2
,
Chandra Kiran Neella
1
1
Department of Chemistry, Palamuru University, Mahbubnagar, Telangana, 509001, India
|
2
Department of Integrated Chemistry, Palamuru University, Mahbubnagar, Telangana, 509001, India
|
Publication type: Journal Article
Publication date: 2023-10-16
scimago Q2
wos Q3
SJR: 0.493
CiteScore: 5.0
Impact factor: 2.5
ISSN: 11440546, 13699261
Materials Chemistry
General Chemistry
Catalysis
Abstract
Herein, an operationally simple temperature-dependant regioselective halogenation of phenols and anilines in water using readily accessible and highly stable Lewis base adducts (LBAs) is reported. These newly discovered LBAs [DBUBr]+Br− and [DBUI]+I− are compatible with a wide range of substrates for regioselective brominations and iodinations with excellent yields (up to 95%), and the products were directly isolated just by filtration and characterized without column chromatographic purification. The organobase DBU was recovered and reused for making corresponding LBAs without a substantial loss of activity. Further halogenations are chemoselective and nucleoselective and proceeded with a very good E-factor. Complimentary regioselectivity (ortho over para) of both aniline and phenol for monohalogenation is a unique feature of the methodology.
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Gavinolla V. et al. A Thermo-regulated Highly Regioselective Mono and Dihalogenations of Phenols and Anilines in Water Employing New Lewis Base Adducts (LBAs) [DBUBr]+Br- and [DBUI]+I- As Green Reagents; A Simple Approach // New Journal of Chemistry. 2023. Vol. 47. No. 45. pp. 20777-20784.
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Gavinolla V., Thangalipalli S., Bandalla S. G., Ramaraju P., Kiran Neella C. A Thermo-regulated Highly Regioselective Mono and Dihalogenations of Phenols and Anilines in Water Employing New Lewis Base Adducts (LBAs) [DBUBr]+Br- and [DBUI]+I- As Green Reagents; A Simple Approach // New Journal of Chemistry. 2023. Vol. 47. No. 45. pp. 20777-20784.
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TY - JOUR
DO - 10.1039/d3nj03370h
UR - https://xlink.rsc.org/?DOI=D3NJ03370H
TI - A Thermo-regulated Highly Regioselective Mono and Dihalogenations of Phenols and Anilines in Water Employing New Lewis Base Adducts (LBAs) [DBUBr]+Br- and [DBUI]+I- As Green Reagents; A Simple Approach
T2 - New Journal of Chemistry
AU - Gavinolla, Vijayalaxmi
AU - Thangalipalli, Swathi
AU - Bandalla, Siddarama Goud
AU - Ramaraju, Panduga
AU - Kiran Neella, Chandra
PY - 2023
DA - 2023/10/16
PB - Royal Society of Chemistry (RSC)
SP - 20777-20784
IS - 45
VL - 47
SN - 1144-0546
SN - 1369-9261
ER -
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BibTex (up to 50 authors)
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@article{2023_Gavinolla,
author = {Vijayalaxmi Gavinolla and Swathi Thangalipalli and Siddarama Goud Bandalla and Panduga Ramaraju and Chandra Kiran Neella},
title = {A Thermo-regulated Highly Regioselective Mono and Dihalogenations of Phenols and Anilines in Water Employing New Lewis Base Adducts (LBAs) [DBUBr]+Br- and [DBUI]+I- As Green Reagents; A Simple Approach},
journal = {New Journal of Chemistry},
year = {2023},
volume = {47},
publisher = {Royal Society of Chemistry (RSC)},
month = {oct},
url = {https://xlink.rsc.org/?DOI=D3NJ03370H},
number = {45},
pages = {20777--20784},
doi = {10.1039/d3nj03370h}
}
Cite this
MLA
Copy
Gavinolla, Vijayalaxmi, et al. “A Thermo-regulated Highly Regioselective Mono and Dihalogenations of Phenols and Anilines in Water Employing New Lewis Base Adducts (LBAs) [DBUBr]+Br- and [DBUI]+I- As Green Reagents; A Simple Approach.” New Journal of Chemistry, vol. 47, no. 45, Oct. 2023, pp. 20777-20784. https://xlink.rsc.org/?DOI=D3NJ03370H.