2012
DOI: 10.1016/j.tet.2012.07.048
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Indium(III) triflate catalysed transacetalisation reactions of diols and triols under solvent-free conditions

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Cited by 32 publications
(39 citation statements)
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“…L-Lactide (LA; TCI; >98.0%) was recrystallized from 1,4-dioxane and then toluene before being dried for more than 3 h. 1,3-Dioxepane (DOP), 2-methyl-1,3-dioxane (MDOX), MDOP, and 2,2-dimethyl-1,3-dioxepane (DMDOP) were synthesized according to previously reported procedures. [28][29][30] ε-Heptanolactone (ε-HepL) was synthesized by Baeyer-Villiger oxidation according to previously reported procedures. 31,32 EtSO 3 H (Aldrich; 95%), PhSO 3 H (TCI; >98.0%), p-toluenesulfonic anhydride (Ts 2 O; Aldrich; 97%), trifluoromethanesulfonic acid (TfOH; Aldrich; >99.0%), bis(trifluoromethanesulfonyl)imide (Tf 2 NH; Wako; 98.0+%), and Ti(OBu) 4 (Alfa Aesar; 99+%) were used without further purification after preparing stock solutions in CH 2 Cl 2 .…”
Section: Methodsmentioning
confidence: 99%
“…L-Lactide (LA; TCI; >98.0%) was recrystallized from 1,4-dioxane and then toluene before being dried for more than 3 h. 1,3-Dioxepane (DOP), 2-methyl-1,3-dioxane (MDOX), MDOP, and 2,2-dimethyl-1,3-dioxepane (DMDOP) were synthesized according to previously reported procedures. [28][29][30] ε-Heptanolactone (ε-HepL) was synthesized by Baeyer-Villiger oxidation according to previously reported procedures. 31,32 EtSO 3 H (Aldrich; 95%), PhSO 3 H (TCI; >98.0%), p-toluenesulfonic anhydride (Ts 2 O; Aldrich; 97%), trifluoromethanesulfonic acid (TfOH; Aldrich; >99.0%), bis(trifluoromethanesulfonyl)imide (Tf 2 NH; Wako; 98.0+%), and Ti(OBu) 4 (Alfa Aesar; 99+%) were used without further purification after preparing stock solutions in CH 2 Cl 2 .…”
Section: Methodsmentioning
confidence: 99%
“…An alternative peroxyacetalization protocol uses aliphatic and aromatic orthoesters as carbonyl sources and indium triflate as Lewis acid catalyst. This method had been reported for transacetalization routes but not previously for the synthesis of perorthoesters 18. Indeed, this process proved to be highly useful for the trans‐peroxyacetalization of 7 with trimethyl orthoacetate (TMOA) as the acetal transfer reagent.…”
Section: Resultsmentioning
confidence: 99%
“…We have recently demonstrated that dehydrative etherification reactions proceed efficiently in the presence of acetals and ketals, an alternative approach that is highly attractive since the carbonyl by-product is far more versatile in terms of its potential to regenerate the acetal species under the reaction conditions (Scheme ). Importantly, In­(OTf) 3 has previously been demonstrated to be a highly efficient catalyst for the generation of acetals and ketals , and for transacetalization reactions, and provides significantly more opportunities for fine-tuning of the reactivity.…”
Section: Results and Discussionmentioning
confidence: 99%