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.
On the basis of the boron-masking strategy, new divalent cross-coupling modules have been designed for the efficient synthesis of boron-substituted oligoarenes. The modules, i.e., monoprotected o-, m-, and p-benzenediboronic acid derivatives, undergo highly selective Suzuki-Miyaura coupling with sp2 iodides, bromides, chlorides, and triflates, affording coupling products in which the protected boronyl groups are left intact.
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
Oligo(quinoline-2,3-diyl)s having a terminal bromo group were synthesized by the Suzuki–Miyaura coupling of 5,8-disubstituted 2-bromoquinolin-3-ylboronic acid derivatives, and their helical structures were elucidated by a single-crystal X-ray analysis of the hexamer, UV measurements, and induction of a non-racemic helical sense by introduction of a chiral end group.
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