Photocatalytic sequential C – H functionalization expediting acetoxymalonylation of imidazo heterocycles

Abstract
The importance of functionalized imidazo heterocycles has often been featured in several impactful research both from academia and industry. Herein, we report a direct C-3 acetoxymalonylation of imidazo heterocycles using relay C–H functionalization enabled by organophotocatalysis starring zinc acetate in the triple role of an activator, ion scavenger as well as an acetylating reagent. The mechanistic investigation revealed a sequential sp2 and sp3 C–H activation, followed by functionalization driven by zinc acetate coupled with the photocatalyst PTH. A variety of imidazo[1,2-a]pyridines and related heterocycles were explored as substrates along with several active methylene reagents, all generating the products with excellent yields and regioselectivity, thus confirming excellent functional group tolerability.

Beilstein J. Org. Chem. 2023, 19, 666–673. doi:10.3762/bjoc.19.48

Source: Beilstein Journal of Organic Chemistry - May 12, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: C – H functionalization imidazo heterocycles photoredox regioselective relay catalysis Letter Source Type: research