Photoinduced Copper-Catalyzed Cross-Coupling of Acylsilanes with Azoles

Published: Jan. 2, 2024

The transition metal-catalyzed direct coupling reac-tions involving electron-rich Fisher carbene species are largely underdeveloped and remain a big chal-lenge. Here, we report reaction of azoles with copper bearing an α-siloxy group, which could be in-situ generated from acylsilanes catalytically under photoirradiation redox-neutral conditions. This features mild conditions remarkable heterocycle compat-ibility. Notably, this protocol tolerates series azole derivatives, including benzoxazole, benzothia-zole, benzoimidazole, benzoisoxazole, oxazole, oxadi-azole, triazolo[4,3-a]pyridine, purine, caffeine etc., is highly synthetic useful in organic synthesis pharmaceutical discovery. Preliminary mecha-nistic studies kinetic analysis implied bimetal-lic relay process.

Language: Английский

Photoinduced Asymmetric Formal Siloxycarbene Insertion into sp³ C–H Bonds Enabled by Chiral Phosphoric Acid

Organic Letters, Journal Year: 2024, Volume and Issue: 26(27), P. 5827 - 5832

Published: July 2, 2024

We disclosed herein an enantioselective formal siloxycarbene insertion reaction enabled by chiral phosphoric acid and blue LED irradiation. This is the first time asymmetric into sp

Language: Английский