Decatungstate-Photocatalyzed Transformations of 2-Bromo-3,3,3-trifluoropropene for Selective Synthesis of
Xiao-Ya Yuan1, Zi-Xuan Lu1, Xianqiang Huang2
1College of Chemistry, School of Life Sciences, Zhengzhou University, Zhengzhou, Henan 450001, China.
Abstract:
Condition-controlled switchable and divergent transformations of cost-effective 2-bromo-3,3,3-trifluoropropene (BTP) and aldehydes were realized using a decatungstate (TBADT)-photocatalyzed strategy. The hydroacylated products, i.e., β,β-Br,CF3-ketones, can be applied as highly functionalized synthetic building blocks for the selective synthesis of (Z/E)-β-CF3-enones. Utilizing this methodology, a broad range of commercially available aromatic and aliphatic aldehydes as well as numerous complex aldehydes, such as lily aldehyde, cyclamen aldehyde, citronellal, vanillin, and aldehydes containing bioactive moieties, including ibuprofen, gemfibrozil, naproxen, flurbiprofen, oleic acid, and aspirin, may be proficiently employed in this transformative process.
Related Concept Videos
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
Thermal and Photochemical Electrocyclic Reactions: Overview
Thermal Electrocyclic Reactions: Stereochemistry
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
E2 Reaction: Stereochemistry and Regiochemistry
When a substrate with two different β hydrogens undergoes an E2 elimination, the presence of a strong base can yield two regioisomeric alkenes. The more-substituted alkene is the major...
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Cycloaddition Reactions: MO Requirements for Photochemical Activation


