Wang J,
Dong Z,
Yang C,
Dong G.
* The University of Chicago, USA
Modular and Regioselective Synthesis of All-Carbon Tetrasubstituted Olefins Enabled
by an Alkenyl Catellani Reaction.
Nat. Chem. 2019;
11: 1106-1112
Key words
Catellani reaction - palladium catalysis - C–H functionalization
Significance
The Dong group reports a general method for the bis-functionalization of alkenes via
a Catellani reaction. This method affords unsymmetrical tetrasubstituted alkenes.
The use of a functionalized norbornene gave high yields and selectivities.
Comment
Utilization of the N-methyl amide-substituted norbornene (N11) was optimal as it gave the highest yield
of product and eliminated the formation of the cyclopropane adduct. A mechanism was
proposed that was supported with detailed kinetic analysis.
