A Catalytic Reaction of Alkynes via Multiple-Site Functionalization

Karur, Subramanian; Kotti, S. R. S. Saibabu; Xu, Xianzhu; Cannon, John F.; Headley, and Allan D.; Li, Guigen

doi:10.1021/ja0304188

Cited by 43 publications

(16 citation statements)

References 23 publications

(14 reference statements)

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“…This reaction was conducted by treating alkynes with N , N ‐dichlorobenzenesulfonamide at 80 °C in the presence of palladium acetate catalyst. The reaction was suggested to go through the formation of β‐halovinyl palladium and π‐allylpalladium species 48…”

Section: Applications Of Vicinal Haloamine Productsmentioning

confidence: 99%

Recent Development of Regio‐ and Stereoselective Aminohalogenation Reaction of Alkenes

2007

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This microreview presents the development of the catalytic aminohalogenation of olefins. The olefin substrates include electron‐deficient and functionalized ones, such as α,β‐unsaturated esters, α,β‐unsaturated ketones and α,β‐unsaturated nitriles. In addition, the first asymmetric aminohalogenation by the use of Evans chiral auxiliaries is also discussed. The convincing evidence is provided to support the aziridinium mechanism of aminohalogenation reaction. The applications of this reaction are described by converting vicinal haloamines into other important synthetic building blocks. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Section: Applications Of Vicinal Haloamine Productsmentioning

confidence: 99%

Recent Development of Regio‐ and Stereoselective Aminohalogenation Reaction of Alkenes

2007

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“…Alkyne functionalization, the addition of functional groups across a triple bond, exemplifies a class of reactions with significant synthetic potential. Accordingly, direct amination reaction of simple alkynes involving general intermolecular C–N bond construction step, such as hydroamiantion 3 4 5 6 , diamination 7 8 , aminooxygenation 9 10 11 12 , aminohalogenation 13 14 and aminoacylation 15 have been successfully developed, during which nucleophilic amination was usually involved with a few strategies employing electrophilic nitrogen sources ( Fig. 1a ).…”

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confidence: 99%

Radical cascade reaction of alkynes with N-fluoroarylsulfonimides and alcohols

et al. 2015

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Cascade reactions initiated by radical addition to alkynes are synthetically very attractive because they enable access to highly complex molecular skeletons in only few synthetic steps under usually mild conditions. Here we report a general radical cascade reaction of alkynes, N-fluoroarylsulfonimides and alcohols, enabling the efficient synthesis of important α-amino-α-aryl ketones from readily available starting materials via a single operation. During this process, the highly regioselective nitrogen-centred radical addition to internal and terminal alkynes generating vinyl radicals and the next explicit migration of aryl group from the nitrogen source lead the following efficient desulfonylation, oxygenation, and semi-pinacol rearrangement. In addition, the semi-pinacol rearrangement precursors, α-alkyloxyl-α,α-diaryl imines, could also be efficiently obtained under milder conditions. This methodology might open a new entry for designing intermolecular radical cascade reaction of alkynes.

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“…As a comparison, the amino‐halogenation of common alkynes are rarely reported . For example, Li's research group developed a Pd‐catalyzed multiple‐site functionalization of alkynes using N , N ‐dichlorobenzenesulfonamide as both N and Cl sources in 2003 (Scheme a) . In the following decade, there were few reports about the aminohalogenation of alkynes.…”

Section: Methodsmentioning

confidence: 99%

Copper Promoted Regio‐ and Stereoselective Aminochlorination of Alkynes and Alkenes with NFSI

Wang

Liu

Chen

et al. 2018

Chemistry A European J

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A simple and rapid copper-promoted aminochlorination of unactivated alkynes and alkenes with N-fluorobenzenesulfonimide (NFSI) was developed. Two series of chloroenamines and chloroamines were obtained in good to high yields. The chlorinated enamines could be obtained in a single E configuration. This reaction involved a radical process and the CuCl acted as the Cl source and NFSI as the N source.

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A Catalytic Reaction of Alkynes via Multiple-Site Functionalization

Cited by 43 publications

References 23 publications

Recent Development of Regio‐ and Stereoselective Aminohalogenation Reaction of Alkenes

Recent Development of Regio‐ and Stereoselective Aminohalogenation Reaction of Alkenes

Radical cascade reaction of alkynes with N-fluoroarylsulfonimides and alcohols

Copper Promoted Regio‐ and Stereoselective Aminochlorination of Alkynes and Alkenes with NFSI

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