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Reactions of a BICAAC with hydroboranes: propensity for Lewis adduct formation and carbene insertion into the B–H bond

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Abstract

The reactivity of a bicyclic (alkyl)(amino)carbene (BICAAC) towards different boranes has been examined in the present work. The reactions with boranes BX3·SMe2 (X = H, Cl, Br), BF3·OEt2 and BCl3 yield Lewis adducts [BICAAC·BH3] (1), [BICAAC·BHCl2] (2), [BICAAC·BH2Cl] (3), [BICAAC·BF3] (4), [BICAAC·BCl3] (5) and [BICAAC·BBr3] (6) respectively, whereas more hydridic boranes, 9-borabicyclo[3.3.1]nonane (9-BBN) and catecholborane (HBcat), enable the insertion of the carbene carbon into the B–H bond to form [BICAAC(H)-(9-BBN)] (7) and [BICAAC(H)-Bcat] (8). These complexes are the first examples of BICAAC–boron compounds and have been characterized using IR, multinuclear NMR spectroscopy, HRMS spectrometry and single crystal X-ray diffraction. Computational analyses were also performed to gain insight into the mechanism of B–H bond activation and adduct formation. Furthermore, the reactions of the BICAAC with boranes have been compared with the known reactions of CAACs and NHCs.

Graphical abstract: Reactions of a BICAAC with hydroboranes: propensity for Lewis adduct formation and carbene insertion into the B–H bond

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Publication details

The article was received on 19 Aug 2019, accepted on 23 Oct 2019 and first published on 23 Oct 2019


Article type: Paper
DOI: 10.1039/C9DT03382C
Dalton Trans., 2019, Advance Article

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    Reactions of a BICAAC with hydroboranes: propensity for Lewis adduct formation and carbene insertion into the B–H bond

    K. K. Manar, V. K. Porwal, R. S. Kamte, M. Adhikari, S. K. Thakur, D. Bawari, A. R. Choudhury and S. Singh, Dalton Trans., 2019, Advance Article , DOI: 10.1039/C9DT03382C

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