Visible-Light-Mediated Solvent-Switched Photosensitizer-Free Synthesis of Polyfunctionalized Quinolines and Pyridines

Hirendra Nath Dhara; Amitava Rakshit; Tipu Alam; Ashish Kumar Sahoo; Bhisma K Patel

doi:10.1021/acs.orglett.2c04027

Visible-Light-Mediated Solvent-Switched Photosensitizer-Free Synthesis of Polyfunctionalized Quinolines and Pyridines

Org Lett. 2023 Jan 27;25(3):471-476. doi: 10.1021/acs.orglett.2c04027. Epub 2023 Jan 13.

Authors

Hirendra Nath Dhara¹, Amitava Rakshit¹, Tipu Alam¹, Ashish Kumar Sahoo¹, Bhisma K Patel¹

Affiliation

¹ Department of Chemistry, Indian Institute of Technology Guwahati, North Guwahati 781039, India.

PMID: 36637219
DOI: 10.1021/acs.orglett.2c04027

Abstract

A solvent (2,2,2-trifluoroethanol (TFE) vs ethyl alcohol (EtOH)) switched synthesis of quinolines and pyridines is illustrated from (E)-2-(1,3-diphenylallylidene)malononitriles via a Pd(II)-catalyzed photochemical process. The active catalyst [L₂Pd(0)] generated serves as an exogenous photosensitizer. The process offers predominantly Z-alkenylated quinolines and pyridines in TFE and EtOH, respectively. Furthermore, large-scale synthesis and a few interesting post-synthetic modifications have been demonstrated.