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