The iterative synthesis of oligoarenes via an organoborane-based cross-coupling reaction (i.e., the Suzuki−Miyaura coupling) has been achieved by using a series of “masked” haloarylboronic acids as building blocks whose ordinarily reactive boronyl groups are temporarily protected by a new masking group derived from 1,8-diaminonaphthalene.

Polyphenyl derivatives Q 0700 Boron-Masking Strategy for the Selective Synthesis of Oligoarenes via Iterative Suzuki-Miyaura Coupling. -A strategy for the iterative cross-coupling uses 1,8-diaminonaphthalene as an efficient masking group for the boronyl group. It is robust enough to avoid undesirable coupling and is easily unmasked by simple treatment with aqueous acids. The synthetic strategy is applied to the synthesis of oligoarene derivatives. -(NOGUCHI, H.; HOJO, K.; SUGINOME*, M.; J. Am. Chem. Soc. 129 (2007) 4, 758-759; Dep. Synth. Chem. Biol. Chem., Grad. Sch. Eng., Kyoto Univ., Nishikyo, Kyoto 615, Japan; Eng.) -Bartels 20-084

Die Benzthiazoliumsalze (I) ergeben bei der Umsetzung mit den Säuren (II) und anschließender Behandlung mit den Alkoholen (III) in guten Ausbeuten die Ester (IV) neben dem Benzthiazol (V).