ACS Catalysis
ACS Catalysis
5 years ago

Experimental Evidence Supporting Related Mechanisms for Ru(II)-Catalyzed Dehydrocoupling and Hydrolysis of Amine-Boranes

Experimental Evidence Supporting Related Mechanisms for Ru(II)-Catalyzed Dehydrocoupling and Hydrolysis of Amine-Boranes
Ainara Telleria, Cristian Vicent, Zoraida Freixa, María A. Garralda, Virginia San Nacianceno
A family of ruthenium(II) half-sandwich complexes was tested for the hydrolytic decomposition of amine-boranes. The analysis of the catalytic results, together with a multilateral approach based on 1H, 11B NMR, and ESI-MS were used to propose a plausible and conceptually unified mechanism for both the hydrolysis and competitive dehydrogenation of amine-boranes. We propose the intermediacy of solvent-stabilized borenium cations during the catalytic cycle, evolving toward dehydrogenation products in distilled THF or releasing amine-hydroxyboranes in aqueous media. Both reaction pathways would liberate up to 1 equivalent of hydrogen through a metal-catalyzed process, but an out-of-cycle low-barrier hydrolysis of amine-hydroxyboranes would produce the 2 additional equivalents of hydrogen in aqueous solutions. Metal-catalyzed deuteration of (non hydrogen-productive) trisubstituted amine-boranes by using D2O as deuterium source was observed, and included as part of the mechanism proposal.

Publisher URL: http://dx.doi.org/10.1021/acscatal.7b02958

DOI: 10.1021/acscatal.7b02958

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