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Sequential Synthesis of Furans from Alkynes: Successive Ruthenium(II)‐ and Copper(II)‐Catalyzed Processes
Author(s) -
Zhang Min,
Jiang HuanFeng,
Neumann Helfried,
Beller Matthias,
Dixneuf Pierre H.
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200805531
Subject(s) - alkyne , catalysis , furan , chemistry , ruthenium , hydrolysis , alcohol , copper , medicinal chemistry , ether , alkyl , organic chemistry
Step in time : 2,5‐Disubstituted furans can be prepared from terminal alkynes in one pot using two successive catalytic reactions (see scheme; p ‐TSA= para ‐toluenesulfonic acid). First, a 1,3‐dienyl alkyl ether is produced by the dimerization of a terminal alkyne and addition of an alcohol catalyzed by [RuCp*(NCMe) 3 ][PF 6 ]. Then, consecutive hydrolysis and cyclization catalyzed by CuCl 2 provides the 2,5‐disubstituted furan.