Article
Suzuki–Miyaura Coupling of Verdazyl Radicals
European Journal of Organic Chemistry
(2017)
Abstract
Halogenated 3-aryl-1,5-diisopropyl verdazyl radicals have been shown to undergo Suzuki–Miyaura coupling reactions with a variety of boronic acids to give biaryl-substituted verdazyl derivatives in acceptable to good yields (50–90 %). The successful coupling depends on the halo substituent and the boronic acid, but most boronic acids could be coupled with the iodophenyl verdazyl radical under either ligandless conditions or in the presence of triphenylphosphine. The successful palladium-catalyzed coupling reaction facilitates the incorporation of verdazyl moieties into conjugated systems and can be used to modify the properties of organic materials. The new radicals were characterized by UV/Vis, ESR, and HRMS analysis and, particularly, by electron impact mass spectrometry, which generated the distinctive verdazyl fragmentation pattern.
Disciplines
Publication Date
February 17, 2017
DOI
10.1002/ejoc.201601483
Publisher Statement
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Citation Information
Thanh-Ngoc Le, Theresa Trevisan, Elizabeth Lieu and David J R Brook. "Suzuki–Miyaura Coupling of Verdazyl Radicals" European Journal of Organic Chemistry Vol. 2017 Iss. 7 (2017) p. 1125 - 1131 ISSN: 1434-193X Available at: http://works.bepress.com/david_brook/30/