Ru(II)-Catalyzed regioselective carbene insertion into β-carbolines and isoquinolines.

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.

Citation

Stephy Elza John, Darshana Bora, Nagula Shankaraiah. Ru(II)-Catalyzed regioselective carbene insertion into β-carbolines and isoquinolines. Organic & biomolecular chemistry. 2022 Jul 27;20(29):5852-5860

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PMID: 35848450

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