期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 24, 期 23, 页码 6019-+出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201800526
关键词
alkynes; carbon dioxide fixation; copper; hydrogenation; rhodium
资金
- DFG [EXC 1069 RESOLV]
- FCI
- DBU
- Carl Zeiss foundation (RCR)
A copper(I) catalyst enables the insertion of carbon dioxide into alkyne C-H bonds by using a suitable organic base with which hydrogenation of the resulting carboxylate salt with regeneration of the base becomes thermodynamically feasible. In the presence of catalytic copper(I) chloride/4,7-diphenyl-1,10-phenanthroline, polymer-bound triphenylphosphine, and 2,2,6,6-tetramethylpiperidine as the base, terminal alkynes undergo carboxylation at 15 bar CO2 and room temperature. After filtration, the ammonium alkynecarboxylate can be hydrogenated to the primary alcohol and water at a rhodium/molybdenum catalyst, regenerating the amine base. This demonstrates the feasibility of a salt-free overall process, in which carbon dioxide serves as a C1 building block in a C-H functionalization.
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