Cobalt-Catalyzed Three-Component Difluoroalkylation–Peroxidation of Alkenes

Chen, Yuanjin; Li, Liangkui; Ma, Yangyang; Li, Zhiping

doi:10.1021/acs.joc.9b00339

Cited by 38 publications

(18 citation statements)

References 72 publications

(29 reference statements)

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“…Based on the results and previous reports, [6,7,8,12] tentative mechanisms were proposed (Scheme 3). DABCO initiated Kornblum‐DeLaMare rearrangement of peroxide 1 generated ketone intermediate A , upon which further elimination of HF afforded the β ‐fluoro enone B .…”

Section: Methodsmentioning

confidence: 65%

Regioselective Synthesis of Emission Color‐Tunable Pyrazolo[1,5‐a]pyrimidines with β,β‐Difluoro Peroxides as 1,3‐Bis‐Electrophiles

Chen

et al. 2021

Adv Synth Catal

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The synthesis and photophysical properties of fluorescent pyrazolo[1,5‐a]pyrimidines (PPs) are explored. An array of 5,7‐disubstituted fluorescent PPs are prepared selectively by using β,β‐difluoro peroxides as the 1,3‐bis‐electrophiles. The synthesized PPs display a fairly significant stokes shift (up to 211 nm) and a large window of tunable emission wavelength that covers most of the visible spectrum (400 nm to 800 nm). Theoretical calculation indicates that the distinguished variation of intramolecular charge transfer (ICT) ability upon the varied substituents is responsible for the color‐tunable fluorescence emission.

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Section: Methodsmentioning

confidence: 65%

Regioselective Synthesis of Emission Color‐Tunable Pyrazolo[1,5‐a]pyrimidines with β,β‐Difluoro Peroxides as 1,3‐Bis‐Electrophiles

Chen

et al. 2021

Adv Synth Catal

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“…Almost at the same time, Li and co‐workers reported the Co(acac) 2 ‐catalyzed three‐component dichloromethylation/peroxidation of alkenes in the presence of Et 3 N in MeCN [30] …”

Section: Di‐ and Trichloromethylation Using Polyhalomethanes As The Pmentioning

confidence: 95%

Recent Advances in Polychloromethylation Reactions

Huang

Pan

2020

Adv Synth Catal

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Molecules with di‐ or trichloromethyl group are widely existed in natural products and man‐made structures that represent special activities in pharmaceuticals and agrochemicals. Besides, polychloromethyl‐containing compounds are also high valuable intermediates in organic synthesis and also can be used as functional materials. Therefore, significant efforts have been made toward the incorporation of polychloromethyl groups into certain structures. In this field, a variety of polychloromethyl reagents, such as CH2Cl2, HCCl3, CCl4, TMSCCl3, TMSCCl2H, etc. have been utilized as the di‐ or trichloromethyl sources toward polychloromethylated structures through radical, nucleophilic, and other reaction patterns. In this review, we summarized and discussed the recent achievements in the synthesis of polychloromethylated compounds, mainly focused on the employment of different polychloromethyl reagents. Most of the works we investigated were reported after 2010. Mechanism discussions and outlooks were also given.

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“…The three-component difluoroalkylation-peroxidation of alkenes with difluorohaloactates and hydroperoxides catalyzed by Co(acac) 2 was developed by the Li group (Scheme 43). 111 Various β-peroxyldifluoroalkyl derivatives were accessed efficiently via this strategy. In addition, other halides were also tolerated in this reaction, giving the alkylation-peroxidation products.…”

Section: Scheme 38mentioning

confidence: 99%