Visible-Light-Driven Reductive Carboarylation of Styrenes with CO₂ and Aryl Halides

Abstract

The first example of visible-light-driven reductive carboarylation of styrenes with CO 2 and aryl halides in a regioselective manner has been achieved. A broad range of aryl iodides and bromides were compatible with this reaction. Moreover, pyridyl halides, alkyl halides and even aryl chlorides were also viable with this method. These findings may stimulate the exploration of novel visible-light-driven Meerwein arylation-addition reactions with user-friendly aryl halides as the radical sources and the photocatalytic utilization of CO 2. File list (2) download file view on ChemRxiv Photo-Meerwein_CO2_Rxiv.pdf (1.13 MiB) download file view on ChemRxiv SI-CO2_Photo-Meerwein_ChemRxiv.pdf (11.82 MiB)

Dendritic fibrous nanosilica-supported dendritic IL/Ru(ii) as photocatalysts for the dicarbofunctionalization of styrenes with carbon dioxide and amines

“…Lately, Martin et al demonstrated the photocatalytic process under visible light between carbon dioxide and alkylcarboxylic acid. [47][48][49][50][51] Considering the possibility of these alterations and our continuing desire for the carboxylation of CO 2 with alkenes for the effectual dicarbofunctionalization reaction, herein, the photoredox-catalyzed a-aminomethylcarboxylation of alkenes with CO 2 and amines is reported. This durable, common, and practical method demonstrates an uncommon sample of the redoxneutral dicarbofunctionalization of alkenes to produce highly efficient g-amino acids under mild reaction circumstances.…”

Photoinduced Hydroarylation and Cyclization of Alkenes with Luminescent Platinum(II) Complexes

“…Since relevant tertiary benzylic radicals were reported to have E red of ca. À1.35 V vs. SCE in MeCN from previous studies, [22] it is expected that the third SET that generates the respective benzylic carbanion should derive from Pt-1C À (E(Pt/Pt À ) = À1.78 V vs. SCE).…”

Utilization of CO2 Feedstock for Organic Synthesis by Visible‐Light Photoredox Catalysis

“…Recently,L ia nd co-workers reported visible-light-driven highly regioselective Meerwein-arylation-type carboxylation of styrenes 48 with readily available aryl halides 49 (X = Cl, Br,I ) under reductivec onditions by using potassium formate (HCO 2 K) as ac heap terminal reductant (Scheme 11 a). [24] Despite much the higher negative reduction potentials of aryl halides, both electron-rich and -poor (hetero)aryl halidesa re well suited for the difunctionalization of electron-deficients tyrenes and a-arylstyrenes to deliver hydrocinnamic acid analogs Allylamine is aw ell-recognized synthetic buildingb lock that containsa na lkene motif with pendent amine nucleophile, amenablef or functionalization. Undoubtedly,i th as occupied a vast domain in organic synthesis.…”