Issue 25, 2021

Formation of amidino-borate derivatives by a multi-component reaction

Abstract

Cyclohexene reacts with the (Fmes)BH2·SMe2 borane reagent and three molar equivalents of the isonitrile CN-Xyl to give the five membered 1,3-BN heterocyclic product 7 that contains a zwitterionic borata-amidinium moiety and a cyclohexenyl substituent. The analogous five-component coupling between cyclopentene, (Fmes)BH2·SMe2 and CN-Xyl in a 1 : 1 : 3 molar ratio gives the related cyclic amidino-borate derivative 10. The reaction of the (Fmes)BH2 derived frustrated Lewis pair 12, in situ generated or employed as the isolated dimer, reacts with 3 CN-Xyl equivs. at elevated temperature (60 °C) to yield the analogous coupling product 13.

Graphical abstract: Formation of amidino-borate derivatives by a multi-component reaction

Supplementary files

Article information

Article type
Paper
Submitted
21 Dzi 2021
Accepted
20 Mud 2021
First published
22 Mud 2021

Org. Biomol. Chem., 2021,19, 5551-5554

Formation of amidino-borate derivatives by a multi-component reaction

J. Li, C. G. Daniliuc, G. Kehr and G. Erker, Org. Biomol. Chem., 2021, 19, 5551 DOI: 10.1039/D1OB00775K

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