A practical and sustainable two-component Minisci alkylation via photo-induced EDA-complex activation. Issue 19 (26th April 2022)

• Record Type: Journal Article
• Authors: Sharique, Mohammed; Majhi, Jadab; Dhungana, Roshan K.; Kammer, Lisa Marie; Krumb, Matthias; Lipp, Alexander; Romero, Eugénie; Molander, Gary A.
• Is Part Of: Chemical science. Volume 13:Issue 19(2022)
• Page Start: 5701
• Page End: 5706
• Publication Date: 2022-04-26
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d2sc01363k
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : An operationally simple, open-air, and efficient light-mediated Minisci C–H alkylation method is described, based on the formation of an electron donor–acceptor (EDA) complex between nitrogen-containing heterocycles and redox-active esters. Abstract : An operationally simple, open-air, and efficient light-mediated Minisci C–H alkylation method is described, based on the formation of an electron donor–acceptor (EDA) complex between nitrogen-containing heterocycles and redox-active esters. In contrast to previously reported protocols, this method does not require a photocatalyst, an external single electron transfer agent, or an oxidant additive. Achieved under mildly acidic and open-air conditions, the reaction incorporates primary-, secondary-, and tertiary radicals, including bicyclo[1.1.1]pentyl (BCP) radicals, along with various heterocycles to generate Minisci alkylation products in moderate to good yields. Additionally, the method is exploited to generate a stereo-enriched, hetereoaryl-substituted carbohydrate.