Aryl C–H amination initiated by laccase-mediated oxidation of 4-phenylurazole

Abstract

A mild amination of aryl C–H initiated by laccase-mediated oxidation of 4-phenylurazole is described.

Asymmetric oxidative Mannich reactions promoted by photocatalysis and electrochemistry

“…Our group has been focusing on the application of the non-natural catalytic function of enzymes in organic synthesis. 28 Some successful examples have been achieved in enzyme-catalyzed asymmetric Mannich reactions. 29…”

Recent Advances in Molecular Oxygen Assisted Laccase Catalyzed Sustainable Organic Transformations

“…Using laccase‐induced oxidation of 4‐phenylurazole, He, Guan and research group generated a new aryl C−H amination strategy [71] . Laccase prefers to oxidize 4‐phenyl‐1,2,4‐triazolidine‐3,5‐dione over anilines, resulting in polarity reversal of the N atoms at the 1 st and 2 nd positions.…”

“…Using laccase-induced oxidation of 4-phenylurazole, He, Guan and research group generated a new aryl CÀ H amination strategy. [71] Laccase prefers to oxidize 4-phenyl-1,2,4-triazolidine-3,5-dione over anilines, resulting in polarity reversal of the N atoms at the 1 st and 2 nd positions. The reported reaction was conducted by taking equimolar amounts of N, N-dimethylaniline, and 4-phenylurazole mildly catalyzed by the laccase from Myceliophthora species.…”

Applications of Microbial Laccases: Patent Review of the Past Decade (2009–2019)

“…A recent review regarding the biocatalytic synthesis of bioactive compounds by laccases was written by Kudanga et al [82], and previously, a thorough review of laccase applications in organic synthesis was presented by Mogharabi and Faramarzi [83]. Recent synthetic efforts include the direct synthesis of furans from aliphatic diallyl ethers through a chemoenzymatic metathesis/aromatization cascade [84], the oxidation of 4-hydroxy-chalcones [85,86], the coupling of coumarins with acetone [87], the whole-cell catalyzed oxidation of 1,4-dihydropyridines [88], a sustainable iodination of phenols [89], the coupling of 4-phenylurazole with a number of aromatic compounds [90], the synthesis of triaminated cyclohexa-2,4-dienones from catechol [91], the synthesis of ferulic acid and ethyl ferulate derivatives [92], hydroxycinnamoyl peptides from ferulic acid and carnosine [93], coumestan derivatives [94], iodinated phenolic compounds [95], caffeic acid dimers [96], ferulic, sinapic, coumaric acid, and -OH dilignol dimers [97], and the oxidation of thioethers to sulfoxides [98]. In WO 2016050988A1, a chemoenzymatic preparation of biphenyl compounds by oxidative coupling is described, and similarly, a synthesis of binaphthyl compounds was reported in CN101418321A.…”