Journal
TETRAHEDRON
Volume 60, Issue 25, Pages 5357-5366Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2004.04.057
Keywords
azulenylboronate; palladium-catalyzed reaction; Miyaura-Suzuki cross-coupling; redox property; violene-cyanine hybrid
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This paper describes an efficient preparation of 2-azulenylboronate (6) starting from 2-iodoazulene by halogen-metal exchange reaction using n-BuLi and subsequent quenching with 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. The boronate 6 has been found to undergo Pd-catalyzed Miyaura-Suzuki cross-coupling reaction with a range of aryl bromides including aromatic poly bromides utilizing Pd-2(dba)(3)-P(t-Bu)(3) as a catalyst and establishes a strategy to produce novel poly(2-azulenyl)benzenes, some of which are found to be insoluble in common organic solvents, however. The redox behavior of 2-arylazulenes and poly(2-azulenyl)benzenes was examined by cyclic voltammetry (CV) and compared with those of 6-azulenylbenzene derivatives reported previously. (C) 2004 Elsevier Ltd. All rights reserved.
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