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Ruthenium(ii)-catalysed 1,2-selective hydroboration of aldazines†
Subham Pradhan,Subramanian Thiyagarajan,Chidambaram Gunanathan
Organic & Biomolecular Chemistry Pub Date : 08/09/2021 00:00:00 , DOI:10.1039/D1OB01218E
Abstract

Herein, an efficient and simple catalytic method for the selective and partial reduction of aldazines using ruthenium catalyst [Ru(p-cymene)Cl2]2 (1) has been accomplished. Under mild conditions, aldazines undergo the addition of pinacolborane in the presence of a ruthenium catalyst, which delivered N-boryl-N-benzyl hydrazone products. Notably, the reaction is highly selective, and results in exclusive mono-hydroboration and desymmetrization of symmetrical aldazines. Mechanistic studies indicate the involvement of in situ formed intermediate [{(η6-p-cymene)RuCl}2(μ-H-μ-Cl)] (1a) in this selective hydroboration.

Graphical abstract: Ruthenium(ii)-catalysed 1,2-selective hydroboration of aldazines
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