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Synfacts 2022; 18(01): 0062
DOI: 10.1055/s-0041-1737211
Metals in Synthesis

The Bönnemann–Wakatsuki Pyridine Synthesis

Contributor(s):
Martin Oestreich
,
Hendrik F. T. Klare
,
Daniel Brösamlen
Bönnemann H, Brinkmann R, Schenkluhn H. Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, Germany
Eine einfache, kobalt-katalysierte Pyridin-Synthese.

Synthesis 1974; 575-577
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Key words

alkynes - cobalt catalysis - nitriles - pyridines - [2+2+2] cycloaddition

Significance

In 1974, Bönnemann and co-workers reported the synthesis of pyridines from nitriles and alkynes by a cobalt(I)-catalyzed [2+2+2] cy­cloaddition. It should be noted that Wakatsuki and Yamazaki independently reported the same transformation using a phosphane-stabilized cobalt(III) complex (Tetrahedron Lett. 1973, 36, 3383).


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Comment

A series of ‘ready-made’ organocobalt complexes and in situ generated catalyst can be employed in this transformation. The anionic ligand Y remains attached at the cobalt center throughout the catalytic cycle, which opens the possibility to optimize the reaction by varying this ‘controlling’ ligand. A comprehensive structure–reactivity study was published by Bönnemann (Angew. Chem., Int. Ed. Engl. 1985, 24, 248).


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Publication History

Article published online:
17 December 2021

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