Photochemical single-step synthesis of β-amino acid derivatives from alkenes and (hetero)arenes

Photocatalytic Deoxygenative Alkylation of C(sp3)−H Bonds Using Sulfonylhydrazones

“…[46][47][48][49][50] Finally, we show that the application of this chemistry provides a preparatively useful route to various medicinally-relevant compounds, such as homobenzylic ethers, aryl ethyl amines, β-amino acids and other moieties which are commonly encountered in approved pharmaceuticals and natural products (Figure 1d). [51][52][53][54][55][56][57] Our experimental investigation began with the optimization of the photocatalytic HAT step.…”

“…Notably, our method provides also immediate access to various β-amino acids, common moieties in many marketed therapeutics (56−61, 35−76%). 54,55 Next, we performed some experiments aimed at elucidating the mechanism of this photochemical alkylative process. The involvement of carbon-centered radicals was confirmed by the presence of adduct 62, obtained upon addition of TEMPO as radical scavenger (Figure 4A).…”

Highly Selective Radical Relay 1,4-Oxyimination of Two Electronically Differentiated Olefins

“…The chemistry of radicals has progressed rapidly in recent years because of such powerful species allowing access to synthetic pathways which are previously considered to be highly challenging or unfeasible. − In this regard, the radical addition across olefins, especially the addition of two radicals, has emerged as an elegant and versatile tool for the straightforward construction of high-value, and often complex, molecular architectures. − Currently, the majority of such reactions focuses on the 1,2-difunctionalization of olefins, simultaneously introducing two functional groups on both sides of the double bond (Figure a). , Apart from this, another type of widely studied radical-involved addition reaction across olefins is radical polymerization (Figure a), being a key synthesis route for obtaining a wide variety of different polymers and composite materials. Despite significant progress, there is still enormous chemical space remaining to be explored in this field.…”

Metal-free photosensitized intermolecular carboimination of alkenes: a green and direct access to both β-amino acids and β-amino ketones

“…During the submission of this independent work, a metal-free photosensitized carboimination of alkenes with oxime carbonates for the synthesis of β-amino acids was reported by the Glorius group. 16 Initially, methyl 2-(((diphenylmethylene)amino)oxy)-2-oxoacetate (1a), obtained easily from readily available alkyl oxalyl chloride and diphenylmethanone oxime, was chosen to explore the intermolecular 1,2-iminocarboxylation of alkenes.…”

“…During the submission of this independent work, a metal-free photosensitized carboimination of alkenes with oxime carbonates for the synthesis of β-amino acids was reported by the Glorius group. 16…”