Simple One Step Syntheses of Indole-3-Acetonitriles From Indole-3-Carboxaldehydes
Fumio Yamada, Tomoko Hashizume, and Masanori Somei
Heterocycles 47(1), 509-516 (1998) (https://www.thevespiary.org/rhodium/Rhodium/chemistry/indole.aldehyde2acetonitrile.html)
(https://www.thevespiary.org/rhodium/Rhodium/chemistry/indole.aldehyde2acetonitrile.html)
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000508709-file_7zuq.gif)
Abstract
One step conversion method of indole-3-carboxaldehydes into indole-3-acetonitriles is developed. Applying the method, 4-nitro- (7a), 4-phenyl- (7b), 4-iodo- (7c), 4-methoxy- (7d), and 4-benzyloxyindole-3-acetonitrile (7e) are available in two steps from indole-3-carboxaldehyde (4).
Edit: Is there anyone out there who would make an educated guess regarding the reaction mechanism, and if this procedure would work for benzaldehydes too, and not just infole-3-aldehydes?