Magic trio: Arynes are easily coupled with neutral nucleophiles and organic bromides to afford functionalized bromoarenes depending upon the nucleophile (Nu). The three‐component coupling proceeds through the formation of bromine ate complexes, and can be applied to the synthesis of multisubstituted isoquinolines and benzo[b]oxepines having pharmacological activity.
Arynes were found to insert into carbon-halogen sigma-bonds of various acid halides, enabling acyl and halogen moieties to be introduced simultaneously into adjacent positions of aromatic rings.
A variety of chlorotriazines were found to undergo insertion of arynes at their carbon–chlorine bonds, leading to formation of triarylated triazines in a straightforward manner.
Insertion reactions O 0288Insertion of Arynes into Carbon-Halogen σ-Bonds: Regioselective Acylation of Aromatic Rings. -The acylation of aromatic rings proceeds via insertion reaction of arynes into carbon-halogen σ-bond of various acid halides (II).The acyl moieties are incorporated ortho to the halogen with perfect regioselectivity. Halogenated arylketones (III) and (V) of structural diversity, whose synthesis would be difficult by conventional methods, can be prepared in a straightforward manner. -(YOSHIDA*, H.; MIMURA, Y.; OHSHITA, J.; KUNAI*, A.; Chem. Commun. (Cambridge) 2007, 23, 2405-2407; Dep. Appl. Chem., Fac. Eng., Hiroshima Univ., Higashi-Hiroshima 739, Japan; Eng.) -M. Paetzel 44-041
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