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Scandium Triflate in Organic Synthesis
Author(s) -
Kobayashi Shū
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199901)1999:1<15::aid-ejoc15>3.0.co;2-b
Subject(s) - chemistry , lewis acids and bases , trifluoromethanesulfonate , scandium , catalysis , lewis acid catalysis , lanthanide , aqueous solution , organic chemistry , nitrogen , medicinal chemistry , ion
Sc(OTf) 3 is a new type of a Lewis acid that is different from typical Lewis acids such as AlCl 3 , BF 3 , SnCl 4 , etc. While most Lewis acids are decomposed or deactivated in the presence of water, Sc(OTf) 3 is stable and works as a Lewis acid in water solutions. Many nitrogen‐containing compounds such as imines and hydrazones are also successfully activated by using a small amount of Sc(OTf) 3 in both organic and aqueous solvents. In addition, Sc(OTf) 3 can be recovered after reactions are completed and can be reused. While lanthanide triflates [Ln(OTf) 3 ] have similar properties, the catalytic activity of Sc(OTf) 3 is higher than that of Ln(OTf) 3 in several cases.