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Chemical Communications

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Hot article: Bonds going for gold!


18 June 2009

Simultaneous cleavage of C-H, C-C and C-C triple bonds under mild conditions has been developed by scientists in Taiwan. 

Rai-Shung Liu and co-workers at the National Tsing-Hua University, in Hsinchu, have reported a gold-catalysed procedure for the oxidative cleavage of aryl-substituted alkynyl ethers using molecular oxygen. 'This work serves the first example that a C-H, single and triple carbon-carbon bonds can be simultaneous cleaved by air at room temperatures with a low loading of catalyst,' explains Liu. 

 

Reaction scheme showing the gold-catalysed simultaneous cleavage of C-H, and single and triple cardon bonds.

 

Previous methods of oxidative cleavage of double or triple bonds using molecular oxygen require high temperatures and additives. Liu's method proceeds under ambient conditions with low catalyst loadings and without any need for a co-catalyst. 'Our new process is environmentally friendly without the cost of energy,' says Liu. 

'This new method provides mechanistic insight into the rapid cleavage of a C-C triple bond,' explains Liu. 'With this new concept, we expect future progress on oxidative cleavage of a double or triple bond under room conditions.' However, a challenging key area would be to replace the gold catalyst as Liu explains, 'gold catalysts are expensive, and the development of a cheap and more efficient catalysts such as Cu(I) will be an important new focus.' 

Mary Badcock 

Link to journal article

Gold-catalyzed oxidative cleavage of aryl-substituted alkynyl ethers using molecular oxygen. Simultaneous degradation of C–H and single and triple carbon–carbon bonds under ambient conditions
Arindam Das, Rupsha Chaudhuri and Rai-Shung Liu, Chem. Commun., 2009, 4046
DOI: 10.1039/b908338c