Ruthenium-Catalyzed Regioselective 1,4-Hydroboration of Pyridines

Ruthenium-Catalyzed Regioselective 1,4-Hydroboration of Pyridines

Simple ruthenium precursor [Ru­(p-cymene)­Cl2]2 1 catalyzed regioselective 1,4-dearomatization of pyridine derivatives using pinacolborane is reported. Two catalytic intermediates, [Ru­(p-cymene)­Cl2Py] 2 and [Ru­(p-cymene)­Cl2(P­(Cy)3)] 3, involved in this process are identified, independently synt...

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Veröffentlicht in:Organic letters 2016-07, Vol.18 (14), p.3402-3405
Hauptverfasser: Kaithal, Akash, Chatterjee, Basujit, Gunanathan, Chidambaram
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container_title Organic letters
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creator Kaithal, Akash
Chatterjee, Basujit
Gunanathan, Chidambaram
description Simple ruthenium precursor [Ru­(p-cymene)­Cl2]2 1 catalyzed regioselective 1,4-dearomatization of pyridine derivatives using pinacolborane is reported. Two catalytic intermediates, [Ru­(p-cymene)­Cl2Py] 2 and [Ru­(p-cymene)­Cl2(P­(Cy)3)] 3, involved in this process are identified, independently synthesized, characterized, and further used directly as effective catalysts; two more catalytic intermediates [Ru­(p-cymene)­Cl2(Py)­(P­(Cy)3)] 4 and [Ru­(p-cymene)­(H)­Cl­(Py)­(P­(Cy)3)] 5 are identified in solution. Complex 5 is the active catalytic intermediate. An intramolecular selective 1,5-hydride transfer in 5 leading to the regioselective 1,4-hydroboration of pyridine compounds is proposed.
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