Palladium-catalysed ligand-free reductive Heck cycloisomerisation of 1,6-en-α-chloro-enamides

Hou, Yachen; Ma, Jing; Yang, Hongyi; Anderson, Edward A.; Whiting, Andrew; Wu, Na

doi:10.1039/c9cc00537d

Cited by 6 publications

(2 citation statements)

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“…Scheme 52 Pd-catalyzed Heck alkenylation of -chloroeneformamides 44A and 52A Wu and co-workers 39 showed, in 2019, that when in situ generated -chloro-N-tosyl-ynamides 53A were submitted to Heck conditions, it led to reduced Heck cyclized products 53B rather than the expected dienes 53C (Scheme 53). Isopropanol is likely to play the role of reducing agent facilitating the in situ formation of palladium hydride.…”

Section: Short Review Synthesismentioning

confidence: 99%

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α-Haloenamides: Synthesis and Subsequent Transformations

Feray¹,

Bertrand²,

galibert³

2022

Synthesis

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Section: Short Review Synthesismentioning

confidence: 99%

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confidence: 99%

α-Haloenamides: Synthesis and Subsequent Transformations

Feray¹,

Bertrand²,

galibert³

2022

Synthesis

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Metal‐Free Oxyacetoxylation of Arylynamines and Ynamides To Construct α‐Acetoxyl Amides

Long

Huang

et al. 2023

Eur J Org Chem

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Ynamides/arylynamines are challenging substrates for oxyacetoxylation, especially due to various reactive sites of the N‐heteroaryl ring. Herein, we report a metal‐free PhI(OAc)2‐mediated oxyacetoxylation of arylynamines/ynamides to provide α‐acetoxyl amides in good to excellent yields. The transformation completes in a short time to afford solely the product in a highly regio‐ and chemo‐selective manner through β‐iodo keteneiminium intermediate, without functionalising the N‐heteroaryl moiety.

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Synthesis of 3-Selenylindoles through Organoselenium-Promoted Selenocyclization of 2-Vinylaniline

et al. 2020

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A novel metal-free one-pot protocol for the synthesis of potential biologically active molecules 3-selenylindoles via intramolecular cyclization/selenylation with simple 2-vinylaniline has been developed with moderate to good yield, thus representing it as a facile route to diverse substitution patterns around the indole core. The reaction proceeded smoothly with a broad substrate scope and excellent functional group tolerance. Moreover, the present synthetic route could be readily scaled up to gram quantity without difficulty. Mechanistic studies have revealed that in situ formed selenium electrophile species may be the key intermediate for the selenocyclization process.

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Palladium-catalysed ligand-free reductive Heck cycloisomerisation of 1,6-en-α-chloro-enamides

Abstract: The first example of an intramolecular hydroarylation of 1,6-en-α-chloro-enamides was achieved by a palladium-catalysed ligand-free reductive Heck cycloisomerisation with no competing Heck-cyclised by-product.

Cited by 6 publications

References 37 publications

α-Haloenamides: Synthesis and Subsequent Transformations

α-Haloenamides: Synthesis and Subsequent Transformations

Metal‐Free Oxyacetoxylation of Arylynamines and Ynamides To Construct α‐Acetoxyl Amides

Synthesis of 3-Selenylindoles through Organoselenium-Promoted Selenocyclization of 2-Vinylaniline

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