New air stable diarylamino substituted diborane(4) derivatives: Synthesis and structures

Abstract

In recent years, the rekindled interest in B/N ring systems has led to a plethora of novel compounds with varying substitution patterns. Diaminodiboranes are the starting compounds for the preparation of many boron compounds such as diborane derivatives, used for many addition and insertion reactions into multiple bonds in the literature, however there are few air-stable diborane(4) derivatives. In this study, to synthesize new air-stable B,B'-diaryl and bis(dimethylamino)-B,B'-diarylaminodiboranes(4), the bulky amines were selected. These derivatives were prepared through the reaction of lithium anilide derivatives and 1,2-dichlorodiboranes. The structures of the compounds were characterized by using nuclear magnetic resonance (NMR) spectroscopy. The crystal and molecular structures of 3ae, 3af, 3bb, 3be, 3ce, 3cd and 3cf were determined using the single-crystal X-ray diffraction technique. X-ray diffraction studies have showed that the diarylamino group in the solid state is nearly orthogonal to the plane due to the boron-bound bulky groups.

Keywords:

• Diborane(4)
• diaminodiboran(4)
• air-stable
• crystal structure
• NMR

Acknowledgements

This study was supported by TÜBİTAK project No. 112T888, by Adnan Menderes University BAP project No. FEF-17004, FEF-16010 and FEF-18009. The authors also acknowledge Dokuz Eylül University for the use of the Rigaku Oxford Xcalibur Eos diffractometer (purchased under University Research Grant no.2010.KB.FEN.13).

Supplementary data

Crystallographic data as .cif files for the structures reported in this paper have been deposited at the Cambridge Crystallographic Data Center with CCDC 1859490, 1859494, 1859493, 1859491, 1859711, 1859492 and 1859495 for 3ae, 3af, 3bb, 3be, 3cd, 3ce and 3cf, respectively. These data can be obtained free of charge via http://www.ccdc.cam.ac.uk/conts/retrieving.html, or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: [phone]; or e-mail: [email protected].