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Issue 2, 2017
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Geminal bis-borane formation by borane Lewis acid induced cyclopropyl rearrangement and its frustrated Lewis pair reaction with carbon dioxide

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Abstract

Cyclopropylacetylene reacts with two molar equivalents of Piers' borane [HB(C6F5)2] under mild conditions by an addition/rearrangement sequence with cyclopropyl ring opening to give a mixture of two α-B(C6F5)2 substituted tetrahydroboroles. This compound forms an active frustrated Lewis pair with PtBu3 that heterolytically splits dihydrogen and adds carbon dioxide as a geminal chelate bis-boryl component. The respective reactions of the two-fold HB(C6F5)2 addition to Ph-CH2CH2C[triple bond, length as m-dash]CH were studied as a geminal Lewis acid reference. Most of the products were characterized by X-ray diffraction.

Graphical abstract: Geminal bis-borane formation by borane Lewis acid induced cyclopropyl rearrangement and its frustrated Lewis pair reaction with carbon dioxide

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Publication details

The article was received on 04 Aug 2016, accepted on 15 Sep 2016 and first published on 16 Sep 2016


Article type: Edge Article
DOI: 10.1039/C6SC03468C
Citation: Chem. Sci., 2017,8, 1097-1104
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    Geminal bis-borane formation by borane Lewis acid induced cyclopropyl rearrangement and its frustrated Lewis pair reaction with carbon dioxide

    Y. Liu, G. Kehr, C. G. Daniliuc and G. Erker, Chem. Sci., 2017, 8, 1097
    DOI: 10.1039/C6SC03468C

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