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It is interesting to note that ethyl 4-methylbenzenesulfinate was isolated as a side product of the reaction. We observed that TsCN is consumed faster in the reaction with catalyst 5 a than in the reaction employing catalyst 6 a. This could explain why the latter is more efficient in the case of the challenging trisubstituted alkene, ketone, and aldehyde (Table 1, entries 8-10). The reaction of TsCN with alcohols is known to give sulfinate esters in the presence of a base such as 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or 1,4-diazabicyclo[2.2.2]octane (DABCO): D. H. R. Barton, J. Cs. Jaszberenyi, E. A. Theodorakis, Tetrahedron 1991, 47, 9167-9178.
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It is interesting to note that ethyl 4-methylbenzenesulfinate was isolated as a side product of the reaction. We observed that TsCN is consumed faster in the reaction with catalyst 5 a than in the reaction employing catalyst 6 a. This could explain why the latter is more efficient in the case of the challenging trisubstituted alkene, ketone, and aldehyde (Table 1, entries 8-10). The reaction of TsCN with alcohols is known to give sulfinate esters in the presence of a base such as 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or 1,4-diazabicyclo[2.2.2]octane (DABCO): D. H. R. Barton, J. Cs. Jaszberenyi, E. A. Theodorakis, Tetrahedron 1991, 47, 9167-9178.
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