Bonds going for gold!
Simultaneous cleavage of C-H, C-C single 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.
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.’
Original publication: Arindam Das, Chem. Commun., 2009.
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