A practical copper-catalyzed approach to β-lactams via radical carboamination of alkenyl carbonyl compounds

Abstract

Functionalized β-lactams are highly important motifs in synthetic chemistry.

Merging Cu-catalysed C–H functionalisation and intramolecular annulations: computational and experimental studies on an expedient construction of complex fused heterocycles

“…Cu(I)/Cu(II)/Cu(III) catalytic cycles have previously been proposed by Zeng and Zhao, albeit operating through a radical process, but encompassing the key Cu(II)/Cu(III) step confirmed in this study. 25 Overall, based on the DFT study, the mechanism depicted in Scheme 4 is proposed to be operative. Initially, the copper coordinates to the substrate, which is followed by C-H bond activation through a CMD step.…”

Transition Metal‐Catalyzed Carboamination of Alkenes and Allenes: Recent Progress

“…A copper‐catalyzed radical carboamination strategy was studied by Zhao and co‐workers for the facile synthesis of β ‐lactams (Scheme 42). [59] Reaction of various β , γ ‐enamides 54 with arenes 26 in presence of DTBP (0.6 mmol), Cu(CH 3 CN) 4 PF 6 (0.02 mmol) furnished desired lactams 85 in good yield and excellent diastereoselectivity (dr‐20 : 1).…”

Copper(i)-catalyzed radical carboamination reaction of 8-aminoquinoline-oriented buteneamides with chloroform: synthesis of-β-lactams

“…Later, on the basis of the reaction of nucleophiles and 8-aminoquinoline-oriented buteneamide compounds in the Engle's research group, 21 our group first used buteneamide compounds as substrates to oxidize toluene with DTBP to generate benzyl radicals, then benzyl radicals attacked inactive double bonds, and coordinated with copper to generate β-lactams successfully. 22 The reaction mode is efficient and can enrich the preparation method of β-lactam. Subsequently, Chen 23 group used cis -3-hexenamide compounds with 8-amino-5-iodoquinoline as the substrates, 4-benzyl Hantzsch esters as the alkyl radical precursor, and rarely used biaryl diphosphine oxide as a chiral ligand to synthesize a series of chiral β-lactam compounds ( Scheme 1b ).…”