Coupling of Epoxides and Lactones by Cationic Indium Catalysts To Form Functionalized Spiro‐Orthoesters. Issue 15 (30th May 2018)

• Record Type: Journal Article
• Authors: Jung, Hyuk‐Joon; Chang, Chen; Yu, Insun; Aluthge, Dinesh C.; Ebrahimi, Tannaz; Mehrkhodavandi, Parisa
• Is Part Of: ChemCatChem. Volume 10:Issue 15(2018)
• Page Start: 3219
• Page End: 3222
• Publication Date: 2018-05-30
• Subjects: epoxides -- expandable monomers -- indium -- lactones -- spiro compounds; Catalysis -- Periodicals; 541.39505
• DOI: 10.1002/cctc.201800474
• Languages: English
• ISSNs: 1867-3880

Abstract

Abstract: We prepared a cationic indium catalyst for the conversion of epoxides and lactones into spiro‐orthoesters (SOEs), a family of expanding monomers. The cationic indium alkyl complexes [(NNi O)In(CH2 SiMe3 )(S)][B{3, 5‐(CF3 )2 C6 H3 }4 ] (2⋅ Solv; H(NNi O)=2, 4‐dicumyl‐6‐({[2‐(dimethylamino)cyclohexyl]imino}methyl)phenol, S=OEt2 or THF) were synthesized and fully characterized. The reaction of ϵ‐caprolactone with 1, 2‐epoxy‐7‐octene resulted in the formation of 2‐(hex‐5‐en‐1‐yl)‐1, 4, 6‐trioxaspiro[4.6]undecane (SOE1) with full conversion of both components. We extended the substrate scope to five‐ and six‐membered lactones as well as to a number of functionalized epoxides. The reactivity of the SOEs was explored. Abstract : The Expandables : A cationic indium catalyst is prepared and evaluated in the conversion of epoxides and lactones into spiro‐orthoesters (SOEs), a family of expanding monomers. We extend the substrate scope to five‐ and six‐membered lactones, as well as to a number of functionalized epoxides. The polymerization of the SOEs is also discussed.