Difunctionalization of alkenes with iodine and <i>tert</i>-butyl hydroperoxide (TBHP) at room temperature for the synthesis of 1-(<i>tert</i>-butylperoxy)-2-iodoethanes

Wang, Hao; Liu, Weibing; Zhu, Zhibo

doi:10.3762/bjoc.13.200

Cited by 27 publications

(13 citation statements)

References 46 publications

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“…Other than above mentioned difunctionalization reactions initiated with C-, N-, O-, P-, and fluorocarbon-radicals, we found a single example of iodo radical-initiated difunctionalization reported by the Zhu group ( Scheme 51 ) [ 85 ]. The reaction of TBHP with I 2 generates t -BuOI and HOI.…”

Section: Other Radical-initiated Reactionsmentioning

confidence: 70%

Difunctionalization of Alkenes and Alkynes via Intermolecular Radical and Nucleophilic Additions

Yao

Zhang

2020

Molecules

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Popular and readily available alkenes and alkynes are good substrates for the preparation of functionalized molecules through radical and/or ionic addition reactions. Difunctionalization is a topic of current interest due to its high efficiency, substrate versatility, and operational simplicity. Presented in this article are radical addition followed by oxidation and nucleophilic addition reactions for difunctionalization of alkenes or alkynes. The difunctionalization could be accomplished through 1,2-addition (vicinal) and 1,n-addition (distal or remote) if H-atom or group-transfer is involved in the reaction process. A wide range of moieties, such as alkyl (R), perfluoroalkyl (Rf), aryl (Ar), hydroxy (OH), alkoxy (OR), acetatic (O2CR), halogenic (X), amino (NR2), azido (N3), cyano (CN), as well as sulfur- and phosphorous-containing groups can be incorporated through the difunctionalization reactions. Radicals generated from peroxides or single electron transfer (SET) agents, under photoredox or electrochemical reactions are employed for the reactions.

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Section: Other Radical-initiated Reactionsmentioning

confidence: 70%

Difunctionalization of Alkenes and Alkynes via Intermolecular Radical and Nucleophilic Additions

Yao

Zhang

2020

Molecules

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“…133 In 2017, Liu, Zhu, and co-workers reported a three-component iodination-peroxidation reaction of styrenes with I 2 and TBHP to produce 1-(tert-butylperoxy)-2-iodoethane derivatives under metalfree conditions ( Table 7, entry 2). 134 In 2019, Chen, Lei, and co-workers developed a vicinal difunctionalization reaction of styrenes with diaryl diselenides and secondary phenylalkylamines by electrochemical synthesis at room temperature that gave -amino selenides ( Table 7, entry 3). 135 In 2017, Fu, Tang, and co-workers reported the three-component hydroxyselenation of styrenes with diphenyl diselenide and water using acidic Ru/HZSM-5-H catalyst ( Table 7, entry 4).…”

Section: Other-atom-centered Radicalsmentioning

confidence: 99%

Radical-Mediated Difunctionalization of Styrenes

Bao¹,

Li²,

Jiang³

et al. 2019

Synthesis

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Styrene, an extremely important compound in the chemical industry, is mainly produced by the dehydrogenation or oxidative dehydrogenation of ethylbenzene. Transformation of this raw organic material to more useful fine organic chemicals is a very significant topic. Recently, the radical difunctionalization of styrene has become a powerful and efficient tool for organic synthesis. This strategy can introduce two substituents into a styrene molecule in one step via addition to the C=C bond, enhancing the molecular complexity in a single operation with good selectivity and wide functional group compatibility.1 Introduction2 C-Centered Radicals3 CF3 and Other Polyfluoroalkyl Radicals4 N-Centered Radicals5 P-Centered Radicals6 O-Centered Radicals7 S-Centered Radicals8 Other-Atom-Centered Radicals9 Conclusion and Perspective

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“…Meanwhile, as simple chemical feedstocks and organic molecules, alkenes have been received widespread attention over the years, owing to their potential for extensive application in organic synthesis . 1,1‐diphenylethylene and their derivatives had been widely used in organic synthesis, particularly, in electrophilic reactions .…”

Section: Introductionmentioning

confidence: 99%

Scandium(III) Trifluoromethanesulfonate Catalyzed Reactions of Donor‐Acceptor Cyclopropanes with 1,1‐Diarylethylenes

Zhu

et al. 2019

ChemistrySelect

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A Lewis acid-promoted DÀ A cyclopropane reacting with 1,1diarylethylenes was developed. This reaction features mild reaction conditions, easy availability of starting materials, good functional group tolerance and high yields (up to 91%).Moreover, substituent effects on product distribution were observed. The scenario of the reaction pathway was supposed to involve the Sc(OTf) 3 -mediated ring-opening 1,3-dipole intermediate followed by the attack of 1,1-diarylethylenes.available donor-acceptor cyclopropanes as versatile reagents. Efforts to develop conditions for the enantioselective reactions of donor-acceptor cyclopropanes, are currently underway. The robustness and practicality of the current method will be further demonstrated by other applications.

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Difunctionalization of alkenes with iodine and tert-butyl hydroperoxide (TBHP) at room temperature for the synthesis of 1-(tert-butylperoxy)-2-iodoethanes

Cited by 27 publications

References 46 publications

Difunctionalization of Alkenes and Alkynes via Intermolecular Radical and Nucleophilic Additions

Difunctionalization of Alkenes and Alkynes via Intermolecular Radical and Nucleophilic Additions

Radical-Mediated Difunctionalization of Styrenes

Scandium(III) Trifluoromethanesulfonate Catalyzed Reactions of Donor‐Acceptor Cyclopropanes with 1,1‐Diarylethylenes

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