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Synfacts 2014; 10(9): 0927
DOI: 10.1055/s-0034-1378602
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Reduce, Rearrange, Reoxidize: Thermal Route to a Ladder Diborole

Contributor(s):
Timothy M. Swager
,
Sibo Lin
Araneda JF, Piers WE, * Sgro MJ, Parvez M. University of Calgary, Canada
Bronsted Acid-Catalyzed Skeletal Rearrangements in Polycyclic Conjugated Boracycles: A Thermal Route to a Ladder Diborole.

Chem. Sci. 2014;
5: 3189-3196
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Further Information

Publication History

Publication Date:
18 August 2014 (online)

 
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Key words

borane reduction - boranes - rearrangement

Significance

Boron-containing polycyclic hydrocarbons are promising molecules for organic electronics. Ladder diborole 2 (previously synthesized in poor yields via photoisomerization) is accessed by Piers and co-workers via stepwise reduction, proton-catalyzed rearrangement, and re-oxidation.


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Comment

To avoid protonolysis of the C–B bonds, 1 is reduced to dianion 3 prior to rearrangement, resulting in a less electrophilic boron center. Although this article focuses specifically on the synthesis of 2, the strategy to reversibly ‘protect’ boranes with excess electrons is innovative and may be applied to the synthesis of other synthetic targets.


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