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Synfacts 2017; 13(09): 0989
DOI: 10.1055/s-0036-1591152
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Parallel Carbonylation and Decarbonylative Heck Reaction on Palladium/Carbon

Contributor(s):
Yasuhiro Uozumi
,
Go Hamasaka
Hattori T. Ueda S. Takakura R. Sawama Y. Monguchi Y. * Sajiki H. * Gifu Pharmaceutical University, Japan
Heterogeneous One-Pot Carbonylation and Mizoroki–Heck Reaction in a Parallel Manner Following the Cleavage of Cinnamaldehyde Derivatives.

Chem. Eur. J. 2017;
23: 8196-8202
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Publication History

Publication Date:
18 August 2017 (online)

 
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Key words

carbonylation - Mizoroki–Heck reaction - cinnamaldehydes - palladium on carbon - palladium catalysis

Significance

Palladium on carbon (Pd/C) catalyzed the carbonylation of aryl iodides with terephthalaldehyde as a CO source to give the corresponding products in up to 98% yield (eq. 1; 17 examples). A simultaneous parallel decarbonylative Mizoroki–Heck reaction of cinnamaldehydes with iodobenzenes (tube A) and carbonylation of 2-iodobenzyl alcohol or 2-iodobenzamide with the CO generated in situ (tube B) were carried out in the presence of Pd/C in an H-shaped tube to give trans-stilbenes and a phthalide or phthalimide, respectively (eq. 2; 6 examples).


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Comment

No recyclability of Pd/C was observed in the parallel decarbonylative Mizoroki–Heck reaction of 4-methoxycinnamaldehyde with iodobenzene and carbonylation of 2-iodobenzyl alcohol (first reuse: 4-methoxy-trans-stilbene: 0% yield; phthalide: trace).


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