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Conventional Tetrakis(triphenylphosphine)palladium‐Copper(I) Iodide‐Catalyzed Sonogashira Coupling of Free and BOC‐ Protected Propargylic Amines “On Water”
Author(s) -
Soberats Bartomeu,
Martínez Luis,
Vega Manuel,
Rotger Carmen,
Costa Antoni
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900240
Subject(s) - sonogashira coupling , chemistry , triphenylphosphine , palladium , aryl , iodide , copper , catalysis , alkynylation , medicinal chemistry , organic chemistry , alkyl
Alkynylation of aryl iodides with propargylic amines has been achieved by means of a Sonogashira coupling using “on water” methods. The use of less than 0.2 mol% of tetrakis(triphenylphosphine)palladium [Pd(PPh 3 ) 4 ] and 1.5 mol% copper(I) iodide [CuI] in the presence of diisopropylethylamine (DIPEA) allows the coupling to proceed at 95 °C yielding moderate to good yields of mono‐, bis‐, and tris‐aminoalkynylbenzene derivatives.