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Metal‐Free Cyclocarboamination of ortho ‐Formyl Phenylacetylenes with Secondary Amines: Access to 1,3‐Diamino‐1 H ‐Indenes and 3‐Amino‐1‐Indanones
Author(s) -
Cui JianFang,
Tang Rishi,
Yang Bin,
Lai Nathanael ChunHim,
Jiang JiaJun,
Deng JieRen,
Wong ManKin
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201801318
Subject(s) - chemistry , amine gas treating , indene , iminium , electrophile , medicinal chemistry , steric effects , combinatorial chemistry , ion , organic chemistry , catalysis
This work first discloses a new strategy for amine activation to give reactive amine anion by in situ generated iminium cation‐amine anion pair through decomposition of sterically hindered aminals. Utilizing this strategy, a highly regio‐ and chemoselective cyclocarboamination of ortho ‐formyl phenylacetylenes with secondary amines has been realized under metal‐free mild reaction conditions. The cyclocarboamination with notably tunable product profiles depends on the separation and purification procedure, a diverse range of 1, 3‐diamino‐1 H ‐indenes (essentially reactive enamines) and 3‐amino‐1‐indanones were obtained, respectively. Moreover, using iodine as an electrophile to couple with various ortho ‐formyl phenylacetylenes and secondary amines, a series of 3‐amino‐2‐iodo‐1‐indanones were efficiently achieved with four bonds (C=O, C−C, C−N and C−I) formation in an one‐pot three‐component reaction. These results demonstrated an unprecedented methodology for the construction of highly functionalized 1 H ‐indene and 1‐indanone compounds.