Direct Access to α-Trifluoromethyl Enones via Efficient Copper-Catalyzed Trifluoromethylation of Meyer–Schuster Rearrangement

Xiong, Ya-Ping; Wu, Mingyue; Zhang, Xiangyu; Ma, Canliang; Huang, Lin; Zhao, Li-Jiao; Tan, Bin; Liu, Xin‐Yuan

doi:10.1021/ol403741m

Cited by 102 publications

(35 citation statements)

References 52 publications

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“…Also in 2014, Bin Tal et al. developed a novel domino copper(I)‐catalyzed trifluoromethylation process that takes place during the M–S rearrangement (Scheme ) . They also used the Togni's reagent II 49 as the CF 3 source, leading to the formation of α‐trifluoromethyl‐α,β‐unsaturated enones 54 from the corresponding propargylic alcohols 55 .…”

Section: Intercepted Meyer–schuster Rearrangementsmentioning

confidence: 99%

Intercepted Meyer–Schuster Rearrangements in Organic Synthesis

2018

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The Meyer-Schuster rearrangement of propargylic alcohols is at ransformation in organic synthesis known for almost ac entury. The products of this reaction-a,b-enones and their a-functionalized units-are highly important functional groups for various synthetic transformations. Two modificationso ft his classical reaction, which involves inter-ceptiono ft he intermediate allenol (or its equivalent) by either electrophiles or nucleophiles, have attracted the attention of synthetic organic chemists. This Focus Review provides ad etailed description of the developmento ft hese two strategies. Intercepted Meyer-Schuster RearrangementsOver the last decade, new variants of the M-S rearrangement of propargylic alcohols 10 (Scheme 3) have been developed to broaden the utility of this classical process in synthetic organic chemistry.T wo of these variants are intercepted (electrophile and nucleophile)M -S rearrangements. These new processes Scheme1.The classicalMeyer-Schusterrearrangement.Scheme2.The Rupe rearrangement.Scheme3.Generalrepresentation of an electrophile-intercepted Meyer-Schuster rearrangement.Scheme4.First reportont he electrophile (halogen)-intercepted Meyer-Schuster rearrangement.Scheme5.Twop ossible mechanistic pathways for the halogen-intercepted Meyer-Schusterr earrangement.Scheme6.Mo-and Au-based cooperative catalysis for the halogen-intercepted Meyer-Schusterr earrangement.Scheme7.Substrate scope of cooperatively Mo-and Au-catalyzed iodo-intercepted Meyer-Schuster rearrangement.Scheme8.HOI-promoted, formaliodo-interceptedM eyer-Schusterr earrangement.Scheme11. Substrate scope for synthesis of a-iodoacrylates.Scheme12. Synthesis of a-iodochalcones from the iodo-intercepted Meyer-Schuster rearrangement of aryl propargylic alcohols.Scheme13. Chloro-intercepted Meyer-Schusterrearrangement by VOCl 3 . Scheme21.Dual Cu-Re-catalyzed CF 3 -intercepted Meyer-Schusterrearrangement.Scheme22. Mechanism for CF 3 -intercepted Meyer-Schusterrearrangement by Cu-Re dual catalysis.Scheme 23. Cu I -catalyzed Z-selective trifluoromethylation during Meyer-Schuster rearrangement.

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Section: Intercepted Meyer–schuster Rearrangementsmentioning

confidence: 99%

Intercepted Meyer–Schuster Rearrangements in Organic Synthesis

2018

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“…[31a,b] Encouraged by these results, Liu andc oworkers developed adomino copper-catalyzed Meyer-Schuster rearrangement/trifluoromethylation reaction, furnishing corresponding a-trifluoromethyl enones (Scheme 9). [32] Both the electronic properties and positions of the substituents had an essential effect on reactivity,g iving products with moderate to good yields. Interestingly,c yclic alcohols were tolerated in this transformation.…”

Section: Trifluoromethylative Rearrangemento Fp Ropargylic Alcoholsmentioning

confidence: 99%

ChemInform Abstract: Recent Advances in the One‐Step Synthesis of Distally Fluorinated Ketones

Zeng

2016

ChemInform

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“…[34] Various propargylic alcohols were transformed to a-trifluoromethylated enone products mainly as E isomersw ith moderate to good yields (Scheme 25). Scope of the trifluoromethylation and dearomatization of alkynes with the Langlois reagent.…”

Section: Oxy-trifluoromethylation Of Alkynesmentioning

confidence: 99%

Recent Developments in the Trifluoromethylation of Alkynes

Gao

Song

Liu

et al. 2015

Chemistry A European J

159

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In the last few years, the development of versatile methodologies to incorporate trifluoromethyl groups into organic molecules has attracted significant attention in synthetic chemistry. This review gives an overview over the development on the trifluoromethylation of alkynes, which have not been solely discussed before. Formation of diverse C(sp, sp(2) , sp(3) )-CF3 bonds are all covered in this review.

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Direct Access to α-Trifluoromethyl Enones via Efficient Copper-Catalyzed Trifluoromethylation of Meyer–Schuster Rearrangement

Cited by 102 publications

References 52 publications

Intercepted Meyer–Schuster Rearrangements in Organic Synthesis

Intercepted Meyer–Schuster Rearrangements in Organic Synthesis

ChemInform Abstract: Recent Advances in the One‐Step Synthesis of Distally Fluorinated Ketones

Recent Developments in the Trifluoromethylation of Alkynes

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