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Volumn , Issue 2, 2009, Pages 193-197

Thieme Chemistry Journal awardees - Where are they now? Synthesis of diamantane-derived N-heterocyclic carbenes and applications in catalysis

(5) Richter, Heinrich a Schwertfeger, Hartmut b Schreiner, Peter R b Fröhlich, Roland a Glorius, Frank a

a UNIVERSITY OF MÜNSTER (Germany)

b JUSTUS LIEBIG UNIVERSITY (Germany)

Author keywords

Diamondoids; N heterocyclic carbene; Organocatalysis; Sonogashira coupling

Indexed keywords

EID: 62349120103 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0028-1087676 Document Type: Article

Times cited : (26)

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- General Procedure for the Synthesis of 1,3-Dialkylimidazolium Tetrafluoroborate Paraformaldehyde (1 equiv) was dissolved in toluene and alkyl amine (1.03 equiv) were added slowly. The mixture was stirred at r.t. for 1 h. After cooling to 0°C another 1.03 equiv of alkyl amine were added. A 3 N solution of HBF4 (1 equiv, 50% in H2O) was added as dropwise and after removal of cooling glyoxal (1 equiv) was added dropwise. The reaction mixture was stirred at 60-75°C for 32-70 h. The solvent was removed under reduced pressure. After column chromatography (SiO2; CH 2Cl2-MeOH, 10:1) the crude product was obtained, which was further purified by recrystallization from CH2Cl2-hexane mixture. 1,3-Diadamantylimidazolium Tetrafluoroborate A total of 0.66 mmol adamantyl amine and 0.32 mmol of other substrates were used. Reaction mixture was stirred for 32 h at 60°C. Yield 95 mg 0.22 mmol, 70
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