6270-17-3Relevant articles and documents
Visible-Light-Induced Multicomponent Synthesis of γ-Amino Esters with Diazo Compounds
Ma, Na,Guo, Lin,Qi, Dan,Gao, Fei,Yang, Chao,Xia, Wujiong
, p. 6278 - 6282 (2021)
A visible-light-induced multicomponent reaction of ethyl diazoacetate, diarylamines, and styrene-type alkenes is described. This novel 1,2-difunctionalization of alkenes can be readily achieved under a simple operation and mild conditions, affording γ-amino esters as major products. The reaction proceeds through the generation of carbon-centered radicals from diazo compounds by a visible-light-promoted proton-coupled electron transfer (PCET) process. The carbon radicals then add to diverse alkenes, delivering new carbon radical species, and the final products are formed with N-centered radicals via a radical-radical coupling.
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Nakamura,E.,Kuwajima,I.
, p. 3368 (1984)
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Copper catalyzed C(sp3)-H bond alkylation via photoinduced ligand-to-metal charge transfer
Treacy, Sean M.,Rovis, Tomislav
supporting information, p. 2729 - 2735 (2021/03/01)
Utilizing catalytic CuCl2 we report the functionalization of numerous feedstock chemicals via the coupling of unactivated C(sp3)-H bonds with electron-deficient olefins. The active cuprate catalyst undergoes Ligand-to-Metal Charge Transfer (LMCT) to enable the generation of a chlorine radical which acts as a powerful hydrogen atom transfer reagent capable of abstracting strong electron-rich C(sp3)-H bonds. Of note is that the chlorocuprate catalyst is an exceedingly mild oxidant (0.5 V vs SCE) and that a proposed protodemetalation mechanism offers a broad scope of electron-deficient olefins, offering high diastereoselectivity in the case of endocyclic alkenes. The coupling of chlorine radical generation with Cu reduction through LMCT enables the generation of a highly active HAT reagent in an operationally simple and atom economical protocol.
Synthesis of Unsymmetrical 1,4-Dicarbonyl Compounds by Photocatalytic Oxidative Radical Additions
Dong, Ya,Li, Ruining,Zhou, Junliang,Sun, Zhankui
, p. 6387 - 6390 (2021/08/23)
Herein we report a photocatalytic oxidative radical addition reaction for the synthesis of unsymmetrical 1,4-dicarbonyl compounds. This reaction utilizes a desulfurization process to generate electrophilic radicals, which add to α-halogenated alkenes and undergo further oxidation to deliver 1,4-dicarbonyl compounds. This mild and highly efficient method provides a valuable alternative to known strategies.
