Japanese researchers have selectively cleaved C-C double and triple bonds in enynes using interactions between alkynes and electrophilic metal salts.

Activation of C-C bonds by transition metal complexes is a challenging area of organic chemistry.  The cleavage of C-C triple bonds is very difficult due to extraordinarily large bond dissociation energies.  With the exception of alkyne-methathesis, catalytic reactions that involve the cleavage of C-C triple bonds are limited and most involve organic fragmentation.  

Naoto Chatani and Kazusa Ota at Osaka University, Japan, have shown for the first time that, a catalytic amount of Rh(II) complex results in skeletal reorganisation of enynes to selectively give cis-configured 1-vinylcycloalkenes, via double cleavage of both double and triple C-C bonds.    

The motivation behind this work was to develop 'a new method of activating unreactive bonds', says Chatani which in turn should open up new fields in organic chemistry.  

Michael Brown