5 years ago

Nickel-Catalyzed Reductive Cycloisomerization of Enynes with CO2

Nickel-Catalyzed Reductive Cycloisomerization of Enynes with CO2
Tianning Diao, Tyler Heitmann, Justin B. Diccianni
Carboxylate groups are ubiquitous in bioactive molecules. The syntheses of carboxylates from petroleum feedstock require a series of oxidation reactions. CO2 represents a cheap and sustainable, preoxidized C1 source. Herein, we describe a simple, selective, and mild procedure for the construction of (hetero)cyclic α,β-unsaturated carboxylic acids from 1,6- and 1,7-enyes and CO2. Terminal 1,7-enynes and sterically hindered alkenes experience a change in regioselectivity and form unconjugated carboxylic acids. Mechanistic studies of the reductive cyclization suggest a hydride insertion pathway, explaining the change in regioselectivity caused by steric effects and distinguishing this work from previous reactions involving CO2.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01034

DOI: 10.1021/acs.joc.7b01034

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