Stereodivergent synthesis of β-iodoenol carbamates with CO₂viaphotocatalysis

Abstract

Photocatalytic conversion of carbon dioxide (CO2) into value-added chemicals is of great significance from the viewpoint of green chemistry and sustainable development. Here, we report a stereodivergent synthesis of β-iodoenol...

E/Z Photoisomerization of Olefins as an Emergent Strategy for the Control of Stereodivergence in Catalysis

“…Qi and Jiang reported the stereodivergent synthesis of β‐iodoenol carbamates using two photocatalysts with different triplet energies in the excited state to control the geometry of the C−C double bond in the final product [28a] . Here, ethynylbenzodioxolones (EBXs) were utilized as starting material in combination with amines and CO 2 (Scheme 4).…”

Updates on hypervalent-iodine reagents: metal-free functionalisation of alkenes, alkynes and heterocycles

“…Mechanistic investigation suggests that the reaction proceeds through a charge transfer complex that might be formed through the halogen bond (Scheme 19). 71…”

“…This journal is © The Royal Society of Chemistry 2022 ceeds through a charge transfer complex that might be formed through the halogen bond (Scheme 19). 71 Recently, Wu et al developed a strategy for the catalytic enantioselective alkynylation of thiazolones (33) and azlactones utilising alkynylethynylbenziodoxolones as an alkynylation reagent. This protocol employs chiral thiourea-phosphonium salt as a catalyst for the synthesis of 4,4-disubstituted thiazolones (34) and azlactones having an alkynyl unit at the quaternary chiral centre.…”

“…102 In 2020, the Volla group reported a visible light-mediated synthesis of azaspiro [4,5]-trienones (72) using acrylamides In the present spirocyclisation, DABSO acts as a "SO 2 " surrogate while diaryliodonium triflates serve as an arylating reagent. The title compound azaspiro [4,5]-trienones (71) were obtained in good yields from the corresponding iodonium salts (Scheme 45). 103 In 2021, Ogura et al reported a TBAF (tetrabutylammonium fluoride) mediated synthesis of a rarely accessible N-alkoxyindolines (74).…”

Base‐Promoted Reaction of Phenols with Spirocylic λ3‐Iodanes: Access to Both 2‐Iodovinyl Aryl Ethers and Diaryl Ethers

“…Copper catalyzed the breaking of iodobenzene bonds of VBXs to obtain cis ‐iodovinyl ethers [18j] and cis ‐iodoenamide [18k] have been successfully developed by the group of Itoh [18j,k] . In 2021, the group of Jiang reported a new method for synthesis of β ‐iodoenol carbamates with CO 2 via photocatalysis [18l] . Although many great achievement have been made in this field, to our knowledge, it is unprecedented that 2‐iodovinyl phenyl ethers were afforded without light, photocatalyst or metal mediating VBXs intermediates to date.…”