Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 22, Pages 15886-15896Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c02898
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- NSFC [21871112, 21971090]
- Graduate Education Innovation Project of Jiangsu Province [KYCX20_2246]
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Tunable electrocatalytic annulation reactions of o-arylalkynylanilines have been established, leading to the green and divergent syntheses of skeletally diverse indoles by adjusting the electrolytes and solvents.
Tunable electrocatalytic annulation reactions of o-arylalkynylanilines have been established, leading to green and divergent syntheses of skeletally diverse indoles by adjusting the electrolytes and the solvents. The presence of ammonium halides as the electrolytes enabled the halogenation of o-arylalkynylanilines to give C3-halogenated indoles whereas naphtho[1',2':4,5]furo[3,2-b]indoles could be obtained by changing the electrolyte from ammonium halides to KI. Interestingly, by combining acetone as the solvent and both NH4I and NH4Cl as the electrolytes, the reaction worked through an intramolecular annulation and [5 + 1] cyclization cascade to form naphtho[1',2':5,6][1,3]oxazino[3,4-a]indoles.
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