The direct decarboxylative allylation of N-arylglycine derivatives by photoredox catalysis

Abstract

The direct decarboxylative allylation of N-arylglycine derivatives has been accomplished via visible-light photoredox catalysis.

Modular Synthesis of Carbon-Substituted Furoxans via Radical Addition Pathway. Useful Tool for Transformation of Aliphatic Carboxylic Acids Based on “Build-and-Scrap” Strategy

“…Initial investigation for divergent furoxan synthesis began with disulfonyl furoxan 2 , which is readily synthesized from α-arylsulfonyl acetic acids in one step , and is not of potentially explosive nature . Inspired by reports of carbon radical addition reactions with a sulfonyl moiety serving as a radical leaving group, − we investigated C–C bond forming reactions of disulfonyl furoxans 2 with carbon radicals (Table S1). To our delight, desired adduct 3a was obtained in high yield using a combination of AgNO 3 and K 2 S 2 O 8 (Figure ).…”

Site-Tunable Csp3–H Bonds Functionalization by Visible-Light-Induced Radical Translocation of N-Alkoxyphthalimides

“…α-Amino acids, well-known radical precursors for decarboxylative radical additions and cross-coupling reactions, reacted quite efficiently under modified reaction conditions (Scheme ). Without any additives, the reaction of N -alkoxyphthalimide 1d with α-amino acids 5 afforded the decarboxylated radical–radical cross-coupling products 6 in moderate yields.…”

Organophotoredox/palladium dual catalytic decarboxylative Csp3–Csp3coupling of carboxylic acids and π-electrophiles

“…In fact, the original method was only operable with a narrow range of 2-substituted allyl electrophiles, while the more challenging 3-substituted allyl electrophiles were not effectively coupled. 5,6,8 Finally, the methods reported thus far utilized iridium-based photosensitizers which are ultimately expensive and unsustainable. 9 Herein, a new organophotoredox/palladium dual catalytic process is described that has greatly improved the utility of this technology through (1) achieving higher yields and greater generality in carboxylic acid nucleophiles, and (2) allowing access to a variety of structurally diverse allylic electrophiles for the installation of various alkenyl, styrenyl, dienyl, and aryl functionalities (Scheme 1C).…”