Conventional Tetrakis(triphenylphosphine)palladium‐Copper(I) Iodide‐Catalyzed Sonogashira Coupling of Free and BOC‐ Protected Propargylic Amines “On Water” | Zendy

Soberats Bartomeu | Zendy; Martínez Luis | Zendy; Vega Manuel | Zendy; Rotger Carmen | Zendy; Costa Antoni | Zendy

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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.

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