Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 34, Pages 10022-10026Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201603352
Keywords
carbon dioxide; copper; fluorine; heterocycles; reaction mechanisms
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Funding
- 1000-Youth Talents Plan
- Sichuan University
- 973 Project from the MOST of China [2015CB856600]
- National Natural Science Foundation of China [21502124]
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Reported is the first oxy-trifluoromethylation of allylamines with carbon dioxide (CO2) using copper catalysis, thus leading to important CF3-containing 2-oxazolidones. It is also the first time CO2, a nontoxic and easily available greenhouse gas, has been used to tune the difunctionalization of alkenes from amino-to oxy-trifluoromethylation. Of particular note, this multicomponent reaction is highly chemo-, regio-, and diastereoselective under redox-neutral and mild reaction conditions. Moreover, these reactions feature good functional-group tolerance, broad substrate scope, easy scalability and facile product diversification. The important products could also be formed with either spirocycles or two adjacent tetrasubstituted carbon centers.
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