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Synfacts 2017; 13(11): 1224
DOI: 10.1055/s-0036-1591387
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Preparation of Monoalkynylpiperidines by Mild Hydrogenation

Contributor(s):
Yasuhiro Uozumi
,
Raghu Nath Dhital
Usuki T. * Komatsu A. Sophia University, Tokyo, Japan
Preparation of Monoalkylpiperidines via the Mild Hydrogenation of Monoalkynylpyridines.

Tetrahedron Lett. 2017;
58: 2856-2858
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Further Information

Publication History

Publication Date:
19 October 2017 (online)

 
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Key words

hydrogenation - Sonogashira coupling - alkynylpiperidines - palladium catalysis - alkynylpyridines

Significance

A series of monoalkynylpyridines were prepared by a Sonogashira coupling (eqs. 1 and 2) in the presence of a Pd catalyst and CuI as a co-catalyst. Hydrogenation of the resulting mono­alkynylpyridines with Pd@C gave the corresponding monoalkylpiperidines in moderate to excellent yields (eq. 3, 7 examples, 43–100% yield).


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Comment

An excess of Pd@C (10 wt% Pd@C, 5 equiv) is necessary to promote the hydrogenation with adequate efficiency under mild conditions (r.t., 1 atm H2, 6 h) in MeOH or AcOH.


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