Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 22, Pages 16134-16143Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c00837
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Funding
- Japan Society for the Promotion of Science (JSPS) [JP19H02735]
- Cooperative Research Program of Network Joint Research Center for Materials and Devices: Dynamic Alliance for Open Innovation Bridging Human, Environment and Materials [20214031]
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A new synthetic method mediated by a B-12 derivative has been developed, which involves aerobic oxygenation to initiate the generation of a carbon-centered radical for the reactive acyl chloride intermediate and subsequent production of cyanoformamides. This method has shown high yields and scalability, with a proposed mechanism based on DFT calculations.
The B-12 derivative, heptamethyl cobyrinate,-mediated electrochemical synthesis of cyanoformamides has been developed. Aerobic oxygenation of the carbon-centered radical initiated in situ generation of the reactive acyl chloride intermediate, which led to cyanoformamides in the presence of an amine. This one-pot and scalable synthetic method has been demonstrated with 41 examples up to 94% yields with 21 new compounds. The mechanism of electrolysis mediated by the B-12 derivative has been proposed based on the DFT calculations.
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