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Updated: Sep 4, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Ru(II)-Catalyzed regioselective carbene insertion into β-carbolines and isoquinolines
Stephy Elza John1, Darshana Bora1, Nagula Shankaraiah1
1Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Hyderabad 500037, India. shankar@niperhyd.ac.in.
Abstract:
A protocol for carbene insertion into the inert C(sp2)-H bond has been established wherein β-carbolines and isoquinolines are explored as intrinsic directing groups. The Ru(II)-catalyzed strategy employing sulfoxonium ylides as the carbene precursor offers an effective and atom-economical functionalization of substrates of biological interest with only DMSO as the sole by-product. The strategy is scalable to gram scale, and it also showcases a wide range of functional group tolerance. ESI-MS studies assisted in the identification of intermediates and consolidation of a probable mechanistic pathway. Furthermore, investigations revealed that the functionalized molecules not only displayed selective inhibition against cancer cell lines, but also demonstrated promising photophysical properties.
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