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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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Article information


Submitted
04 Aug 2016
Accepted
15 Sep 2016
First published
16 Sep 2016

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2017,8, 1097-1104
Article type
Edge Article

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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