Visible‐Light‐Induced Three‐Component Intermolecular Trifluoromethyl‐Alkenylation Reactions of Unactivated Alkenes

Guo, Yuanqiang; Wang, Ruiguo; Song, Hongjian; Liu, Yuxiu; Wang, Qingmin

doi:10.1002/adsc.202001434

Cited by 24 publications

(15 citation statements)

References 83 publications

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“…139 Guo et al also applied trifluoromethylation strategy to functionalize unactivated alkenes and form, upon addition to vinyl sulfones, styrene-based activated olefines. 140 Through this strategy, the trifluoromethylation scope was therefore broadened to the formation of unsaturated bonds.…”

Section: Other Mechanismsmentioning

confidence: 99%

Multicomponent reactions and photo/electrochemistry join forces: atom economy meets energy efficiency

et al. 2022

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Section: Other Mechanismsmentioning

confidence: 99%

Multicomponent reactions and photo/electrochemistry join forces: atom economy meets energy efficiency

et al. 2022

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“…Very recently, Wang's group described a mild, practical, visible-light-induced protocol for the intermolecular threecomponent alkenylation/alkynylation of Langlois' reagent (CF 3 SO 2 Na, 51-15), olefins, and unsaturated sulfones (Scheme 51E). 189 The trifluoromethyl group could be introduced in the styrene/alkyne-based products in moderate to good yields. The nascent CF 3 radical was formed through a single-electrontransfer reaction between photoexcited Ir-photocatalyst and CF 3 SO 2 Na.…”

Section: Radical-mediated Desulfonylation Of Vinylic Sulfonesmentioning

confidence: 99%

Desulfonylation via Radical Process: Recent Developments in Organic Synthesis

et al. 2021

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As the "chemical chameleon", sulfonyl-containing compounds and their variants have been merged with various types of reactions for the efficient construction of diverse molecular architectures by taking advantage of their incredible reactive flexibility. Currently, their involvement in radical transformations, in which the sulfonyl group typically acts as a leaving group via selective C−S, N−S, O−S, S−S, and Se−S bond cleavage/ functionalization, has facilitated new bond formation strategies which are complementary to classical two-electron cross-couplings via organometallic or ionic intermediates. Considering the great influence and synthetic potential of these novel avenues, we summarize recent advances in this rapidly expanding area by discussing the reaction designs, substrate scopes, mechanistic studies, and their limitations, outlining the state-of-the-art processes involved in radical-mediated desulfonylation and related transformations. With a specific emphasis on their synthetic applications, we believe this review will be useful for medicinal and synthetic organic chemists who are interested in radical chemistry and radical-mediated desulfonylation in particular. CONTENTS

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“…), no further development of this topic took place until 2017. Since then, a number of diverse alkynyltrifluoromethylation protocols have been published [17][18][19][20][21][22][23][24][25][26][27] including enantioselective transformations. [25,26] The aim of the current minireview is to summarize the development of alkynyltrifluoromethylation reactions.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

“…), no further development of this topic took place until 2017. Since then, a number of diverse alkynyltrifluoromethylation protocols have been published [17][18][19][20][21][22][23][24][25][26][27] including enantioselective transformations. 25,26 Scheme 1 Organofluorine drugs: examples with benefits of fluorination Dieses Dokument wurde zum persönlichen Gebrauch heruntergeladen.…”

Section: Introductionmentioning

confidence: 99%

Developments in the Alkynyltrifluoromethylations of Alkenes and Alkynes

et al. 2022

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As a consequence of the expanding relevance of fluorine-containing organic molecules in drug research, the synthesis of organofluorine scaffolds has received high significance in synthetic organic chemistry. Trifluoromethylative difunctionalizations of carbon–carbon multiple bonds, with the simultaneous introduction of a CF3 group and another function, have considerable potential. Considering the high importance of carbon–carbon bond-forming reactions in organic synthesis, carbotrifluoromethylations and, in particular, alkynyltrifluoromethylations are considered to be increasing areas of synthetic chemistry. Alkynyltrifluoromethylation is a narrow segment and a relatively new approach in synthetic chemistry, however it has not been reviewed so far. Therefore, our goal in the current minireview is to summarize the recent developments of alkynyltrifluoromethylation reactions taking into consideration several main aspects, such as (a) alkynyltrifluoromethylation reactions of alkenes including (i) reactions involving intramolecular alkynyl migration and (ii) intermolecular transformations as well as (b) alkynyltrifluoromethylation reactions of alkynes.

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Visible‐Light‐Induced Three‐Component Intermolecular Trifluoromethyl‐Alkenylation Reactions of Unactivated Alkenes

Cited by 24 publications

References 83 publications

Multicomponent reactions and photo/electrochemistry join forces: atom economy meets energy efficiency

Multicomponent reactions and photo/electrochemistry join forces: atom economy meets energy efficiency

Desulfonylation via Radical Process: Recent Developments in Organic Synthesis

Developments in the Alkynyltrifluoromethylations of Alkenes and Alkynes

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