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Direct Substitution of the Hydroxy Group at the Allylic/propargylic Position with Carbon‐ and Heteroatom‐ centered Nucleophiles Catalyzed by Yb(OTf) 3
Author(s) -
HUANG Wen,
SHEN QuanSheng,
WANG JiaLiang,
ZHOU XiGeng
Publication year - 2008
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200890136
Subject(s) - chemistry , heteroatom , allylic rearrangement , nucleophile , catalysis , methylene , environmentally friendly , carbon fibers , substitution reaction , organic chemistry , group (periodic table) , leaving group , combinatorial chemistry , medicinal chemistry , ring (chemistry) , ecology , composite material , biology , materials science , composite number
An efficient and highly selective Yb(OTf) 3 ‐catalyzed direct substitution of the hydroxy group at the allylic and propargylic positions with a variety of heteroatom‐ and carbon‐centered nucleophiles, such as alcohols, thiols, amines, amides and active methylene compounds has been developed. The advantages of the present catalytic system are wide availability of the starting materials, especially for tolerance to thiols, no need for dried solvents and additives, mild conditions, short time of reaction, simple manipulation and environmentally friendly catalyst that can be recovered and reused at least ten times without significant reduction of activity.