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Synthesis of 3‐Alkynylselenophene Derivatives by a Copper‐Free Sonogashira Cross‐Coupling Reaction
Author(s) -
Alves Diego,
dos Reis Joel S.,
Luchese Cristiane,
Nogueira Cristina W.,
Zeni Gilson
Publication year - 2008
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/ejoc.200700707
Subject(s) - sonogashira coupling , chemistry , aryl , coupling reaction , catalysis , alkyl , copper , base (topology) , organic chemistry , combinatorial chemistry , medicinal chemistry , polymer chemistry , palladium , mathematical analysis , mathematics
3‐Iodoselenophene derivatives undergo direct Sonogashira cross‐coupling reactions with several terminal alkynes in the presence of a catalytic amount of Pd(PPh 3 ) 2 Cl 2 in DMF with Et 3 N as the base under cocatalyst‐free conditions. This cross‐coupling reaction proceeded cleanly under mild conditions and was performed with propargylic alcohols and propargylic ethers, as well as alkyl, vinyl and aryl alkynes to furnish the corresponding 3‐alkynylselenophenes in good‐to‐excellent yields.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)