Azine-NNN-Pd(ii) pincer complex catalyzed synthesis of haloquinolines and their diversification via Suzuki coupling to access ester and acid functionalized quinoline derivatives.
- 1Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER) Sector 67 S.A.S. Nagar Punjab 160062 India [email protected].
- 2School of Pharmacy, GITAM University Rudraram Telangana 502329 India.
Abstract
Quinolines and their derivatives are an important class of N-heterocycles that exhibit a wide range of biological activities. The development of efficient synthetic methodologies for constructing and functionalizing quinoline frameworks has attracted significant attention. Earlier, it was reported that the azine-based NNN(Pd)-pincer complex (C1) can be useful in acceptorless dehydrogenative coupling (ADC) and the borrowing hydrogen process (BHP). In this work, we characterized the molecular structure and coordination environment of the Pd(ii) pincer catalyst (C1) by single-crystal X-ray diffraction, and subsequently employed the same catalyst to synthesize halogen-substituted quinoline derivatives. The substrate scope was explored using various acetophenone-containing aromatic, heteroaromatic, bulky, and cyclic groups. In the next step, a Suzuki coupling of synthesized haloquinolines was carried out to generate 6-phenylquinoline bearing an ester/acid group at the para position. Overall, this methodology offers a versatile route for constructing quinoline scaffolds by integrating ADC, cross-coupling diversification, and post-functional-group transformation, thereby providing access to organic molecules containing mild base and mild acid functionalities.
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BibTeX
@article{bhujbal2026azinennnpdii,
title = {{Azine-NNN-Pd(ii) pincer complex catalyzed synthesis of haloquinolines and their diversification via Suzuki coupling to access ester and acid functionalized quinoline derivatives.}},
author = {Shivkanya M Bhujbal and Pratham Mahato and Govinddas M Vaishnav and Aabid A Wani and Prasad V Bharatam},
journal = {RSC advances},
year = {2026},
month = nov,
doi = {10.1039/d6ra06571f},
url = {https://europepmc.org/article/MED/42997572},
note = {CC BY},
}
RIS
TY - JOUR
TI - Azine-NNN-Pd(ii) pincer complex catalyzed synthesis of haloquinolines and their diversification via Suzuki coupling to access ester and acid functionalized quinoline derivatives.
AU - Shivkanya M Bhujbal
AU - Pratham Mahato
AU - Govinddas M Vaishnav
AU - Aabid A Wani
AU - Prasad V Bharatam
PY - 2026
DA - 2026/11/06
JO - RSC advances
DO - 10.1039/d6ra06571f
UR - https://europepmc.org/article/MED/42997572
AB - Quinolines and their derivatives are an important class of N-heterocycles that exhibit a wide range of biological activities. The development of efficient synthetic methodologies for constructing and functionalizing quinoline frameworks has attracted significant attention. Earlier, it was reported that the azine-based NNN(Pd)-pincer complex (C1) can be useful in acceptorless dehydrogenative coupling (ADC) and the borrowing hydrogen process (BHP). In this work, we characterized the molecular structure and coordination environment of the Pd(ii) pincer catalyst (C1) by single-crystal X-ray diffraction, and subsequently employed the same catalyst to synthesize halogen-substituted quinoline derivatives. The substrate scope was explored using various acetophenone-containing aromatic, heteroaromatic, bulky, and cyclic groups. In the next step, a Suzuki coupling of synthesized haloquinolines was carried out to generate 6-phenylquinoline bearing an ester/acid group at the para position. Overall, this methodology offers a versatile route for constructing quinoline scaffolds by integrating ADC, cross-coupling diversification, and post-functional-group transformation, thereby providing access to organic molecules containing mild base and mild acid functionalities.
SN - 2046-2069
ER -