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Synfacts 2013; 9(1): 0044
DOI: 10.1055/s-0032-1317883
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Synthesis of New Borolylbenzenes

Contributor(s):
Timothy M. Swager
,
Gregory D. Gutierrez
Braunschweig H, * Chiu C.-W, Damme A, Engels B, Gamon D, Hörl C, Kupfer T, Krummenacher I, Radacki K, Walter C. Julius-Maximilians-Universität Würzburg, Germany and National Taiwan University, Tapei, Taiwan
Oligo(borolyl)benzenes–Synthesis and Properties.

Chem. Eur. J. 2012;
18: 14292-14304
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Publication History

Publication Date:
17 December 2012 (online)

 
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Key words

oligoboroles - organoboron compounds

Significance

The synthesis and properties of a new class of oligoboroles are reported. These compounds represent the first examples of antiaromatic borolyl moieties connected by an organic π-conjugated system (i.e. benzene) and are synthesized via tin–boron exchange. Adducts of the oligoboroles with various pyridine derivatives and their hexaanion salts with magnesium and lithium are reported and extensively studied.


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Comment

The Lewis acidities of boroles B and C are assessed by base-transfer studies with a pentaphenylborole–3,5-lutidine adduct. The authors conclude that there is an effective electronic communication between the para-functionalized borolyl groups of C because its double adduct is not observed during the exchange experiment. However, base-transfer studies of B indicate the formation of both single and double adducts, thus suggesting less interaction between the meta-substituted boroles.


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