We report a cationic indium catalyst for the conversion of epoxides and lactones to spiro-orthoesters, a family of expanding monomers. The cationic indium alkyl complexes [(NNiO)In(CH2SiMe3)(S)][B(3,5-(CF3)2C6H3)4] (2•S; S = OEt2 or THF) were synthesized and fully characterized. The reaction of ε-caprolactone and 1,2-epoxy-7-octene forms 2-(hex-5-en-1-yl)-1,4,6-trioxaspiro[4.6]undecane (SOE1) with full conversion of both components. We can expand the substrate scope to 5 and 6 membered lactones as well as a number of functionalized epoxides. The further reactivity of the SOEs is discussed.
Publications
(59) Phys. Fluids 2021, 33, 043102
(58) Phys. Fluids 2021, 33, 032010
(57) Polym. Chem. 2021, 12, 783 - 806
(56) Catal. Sci. Technol. 2021, 11, 2119–2129
(55) Catal. Sci. Technol. 2021, 11, 62-91
(54) ACS Appl. Mater. Interfaces 2020, 12, 52182−52191
(53) Macromolecules 2020, 53(20), 8819-8828
(52) ACS Catal. 2020, 10, 6488−6496
(51) Chem. Sci. 2020, 11, 6485−6491
(50) Inorg. Chem. 2020, 59, 5546−5557
(49) Chem. Commun. 2019, 55, 3347-3350
(48) Coord. Chem. Rev. 2019 380, 35–57
(47) ChemCatChem 2018, 10, 3219 – 3222
(46) ACS Sustainable Chem. Eng., 2018, 6, 1650–1661
(45) Acc. Chem. Res. 2017, 50, 2861−2869
(44) J. Rheol. 2017 61(6), 1137-1148
(43) ACS Catal. 2017, 7, 6413−6418
(42) Dalton Trans. 2017 46, 6723–6733
(41) Macromolecules 2017 50 (6), 2535–2546
(40) Inorg. Chem. 2017 56 (3), 1375–1385
(39) Macromolecules 2016 49 (23), 8812–8824
(38) Inorg. Chem. 2016, 55(18), 9445–9453
(37) Inorg. Chem. 2016, 55(11), 5365–5374
(36) Macromolecules 2016, 49(3), 909–919
(35) Macromolecules 2015, 48(18), 6672-6681
(34) Chem. Sci., 2015, 6, 5284–5292
(33) Dalton Trans. 2015, 44, 14248 - 14254
(32) Dalton Trans. 2015, 44, 6126 - 6139
(31) Inorg. Chem. 2014, 53(18), 9897−9906
(30) J. Am. Chem. Soc. 2014, 136(32), 11264–11267
(29) Inorg. Chem. 2014, 53(13), 6828–6836
(28) Organometallics 2013, 32(23), 6950–6956
(27) Macromolecules 2013, 46, 3965−3974
(26) Chem. Commun. 2013, 49, 4295-4297
(25) J. Am. Chem. Soc. 2012, 134(30), 12758–12773
(24) Chem. Commun. 2012, 48(54), 6806-6808
(23) Polymer 2012, 53(12), 2443-2452
(22) Dalton Trans. 2012, 41(26), 8123-8134.
(21) Rheol. Acta 2012, 51(4), 357-369
(20) J. Am. Chem. Soc. 2011, 133(24), 9278–9281
(19) J. Rheol. 2011, 55(5), 987-1004
(18) Organometallics 2010, 29(22), 6065–6076
(17) Inorg. Chem. 2010, 49(12), 5444–5452
(16) Dalton Trans. 2010, 39(2), 541–547
(15) J. Supercrit. Fluids 2010, 51(3), 376-383
(14) Organometallics 2009, 28(21), 6370–6373
(13) Organometallics 2009, 28(13), 3889–3895
(12) Organometallics, 2009, 28(5), 1309-1319
(11) Angew. Chem. Int. Ed. 2008, 47(12), 2290-2293