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2005
Alkynes
Q 0087
27- 072
A Convenient Synthesis of Functionalized 1-Aryl-1,3-alkadiynes. — A novel convenient approach towards title arylalkadiynes (III), (V) is presented, involving lithiation—rearrangement of alkadiynes like (I) followed by Sonogashira coupling towards
aryl iodides (II) and (IV), respectively. A wide variety of functionalized aryl iodides
can take part in this reaction while aryl bromides are inert [cf. (IVb)]. In the reaction of
electron-rich aryl iodides or polyhaloarenes, the ethylenediamine generated during
lithiation must be removed before adding the Pd catalyst to avoid complexation reactions. — (BALOVA*, I. A.; SOROKOUMOV, V. N.; MOROZKINA, S. N.;
VINOGRADOVA, O. V.; KNIGHT, D. W.; VASILEVSKY, S. F.; Eur. J. Org. Chem.
2005, 5, 882-888; Dep. Org. Chem., St. Petersburg State Univ., St. Petersburg 198504,
Russia; Eng.) — Mischke
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