Xu, Bin published the artcilePhotocatalyzed Diastereoselective Isomerization of Cinnamyl Chlorides to Cyclopropanes, Formula: C8H5IO, the publication is Journal of the American Chemical Society (2020), 142(13), 6206-6215, database is CAplus and MEDLINE.
Endergonic isomerizations are thermodynamically unfavored processes that are difficult to realize under thermal conditions. A photocatalytic and diastereoselective isomerization of acyclic cinnamyl chlorides to strained cyclopropanes is reported. Quantum mech. calculations (uM06-2X and DLPNO), including TD-DFT calculations, and exptl. studies provide evidence for the energy transfer from an iridium photocatalyst to the allylic chloride substrate followed by C-Cl homolytic cleavage. Subsequent Cl• radical migration forms a localized triplet 1,3-diradical intermediate that, after intersystem crossing, undergoes ring-closing to form the desired product. The mild reaction conditions are compatible with a broad range of functional groups to generate chlorocyclopropanes in high yields and diastereoselectivities. A more efficient process is developed by addition of a catalytic amount of a nickel complex, and we propose a novel role for this cocatalyst to recycle an allyl chloride byproduct generated in the course of the reaction. The reaction is also shown to be stereoconvergent, as an E/Z mixture of cinnamyl chlorides furnish the anti-chlorocyclopropane product in high diastereoselectivity. The use of a visible light activated photocatalyst to transform substrates in combination with a transition metal catalyst to recycle byproducts back into the catalytic cycle will provide unique opportunities for the discovery of new reactivity is anticipated.
Journal of the American Chemical Society published new progress about 69626-75-1. 69626-75-1 belongs to benzofurans, auxiliary class Iodide,Benzofuran, name is 2-Iodobenzofuran, and the molecular formula is C15H12O6, Formula: C8H5IO.
Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem