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Synfacts 2020; 16(02): 0165
DOI: 10.1055/s-0039-1691607
Metals in Synthesis
© Georg Thieme Verlag Stuttgart · New York

Regioselective Synthesis of Tetrasubstituted Olefins via an Alkenyl Catellani Reaction

Contributor(s):
Mark Lautens
,
Austin D. Marchese
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
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Publication History

Publication Date:
21 January 2020 (online)

 
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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.


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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.


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