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Title: Metal-free cyclocarboamination of ortho-formyl phenylacetylenes with secondary amines : access to 1,3-diamino-1H-indenes and 3-amino-1-indanones
Authors: Cui, JF 
Tang, R 
Yang, B 
Lai, NCH 
Jiang, JJ 
Deng, JR 
Wong, MK 
Issue Date: 1-Feb-2019
Source: Advanced synthesis & catalysis, 1 Feb. 2019, v. 361, no. 3, p. 569-577
Abstract: 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-1H-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 1H-indene and 1-indanone compounds. (Figure presented.).
Keywords: Aminal
Amine activation
Carboamination
Indanone
Indene
Publisher: Wiley-VCH
Journal: Advanced synthesis & catalysis 
ISSN: 1615-4150
EISSN: 1615-4169
DOI: 10.1002/adsc.201801318
Rights: © 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
This is the peer reviewed version of the following article: Cui, J. F., Tang, R., Yang, B., Lai, N. C. H., Jiang, J. J., Deng, J. R., & Wong, M. K. (2019). Metal‐free cyclocarboamination of ortho‐formyl phenylacetylenes with secondary amines: Access to 1, 3‐diamino‐1H‐indenes and 3‐amino‐1‐indanones. Advanced Synthesis & Catalysis, 361(3), 569-577, which has been published in final form at https://doi.org/10.1002/adsc.201801318. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
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