Visible light-induced chemoselective 1,2-diheteroarylation of alkenes.

Guo, Shi-Yu; Liu, Yi-Peng; Huang, Jin-Song; He, Li-Bowen; He, Gu-Cheng; Ji, Ding-Wei; Wan, Boshun; Chen, Qing-An · Nat Commun · 2024

basic_science · Level V

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Abstract

Visible-light photocatalysis has evolved as a powerful technique to enable controllable radical reactions. Exploring unique photocatalytic mode for obtaining new chemoselectivity and product diversity is of great significance. Herein, we present a photo-induced chemoselective 1,2-diheteroarylation of unactivated alkenes utilizing halopyridines and quinolines. The ring-fused azaarenes serve as not only substrate, but also potential precursors for halogen-atom abstraction for pyridyl radical generation in this photocatalysis. As a complement to metal catalysis, this photo-induced radical process with mild and redox neutral conditions assembles two different heteroaryl groups into alkenes regioselectively and contribute to broad substrates scope. The obtained products containing aza-arene units permit various further diversifications, demonstrating the synthetic utility of this protocol. We anticipate that this protocol will trigger the further advancement of photo-induced alkyl/aryl halides activation.