Synthesis of ladder-type π-conjugated heteroacenes via Palladium-catalyzed double N-arylation and intramolecular O-arylation

K Kawaguchi, K Nakano, K Nozaki

Index: Kawaguchi, Keiko; Nakano, Koji; Nozaki, Kyoko Journal of Organic Chemistry, 2007 , vol. 72, # 14 p. 5119 - 5128

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Citation Number: 118

Abstract

Ladder-type heteroacenes containing pyrrole or furan rings, indolo [3, 2-b] carbazoles and dibenzo [d, d'] benzo [1, 2-b: 4, 5-b'] difurans, were effectively synthesized from the common intermediates, 2, 5-bis (o-chloroaryl) hydroquinones. The key reactions are palladium- catalyzed double N-arylation of aniline and intramolecular O-arylation, which enable regioselective ring closure. In addition to the parent indolo [3, 2-b] carbazole and dibenzo [ ...