Regio‐ and Stereospecific 1,3‐Allyl Group Transfer Triggered by a Copper‐Catalyzed Borylation/<i>ortho</i>‐Cyanation Cascade

Yang, Yang

doi:10.1002/anie.201508294

Cited by 37 publications

(15 citation statements)

References 62 publications

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“…Yang [48] recognised the potential of the dearomatized intermediates to undergo rearomatization-driven sigmatropic rearrangement and disclosed ac atalytic borylation/orthocyanation/Cope rearrangement sequence (Scheme 16 A). After the initial borocupration and ortho-cyanation (vide supra), pre-installed allyl chains at the C1 position of 2-vinylnaphthalene derivatives 52 migrate to the benzylic position in a[ 3,3]-sigmatropic Cope rearrangement to re-establish aromaticity without the need for an alkoxide-assisted [1,3]-H shift (see int-15,Scheme 16 A).…”

Section: Allenesmentioning

confidence: 99%

Copper‐Catalyzed Borylative Couplings with C−N Electrophiles

et al. 2020

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Scheme 13. Montgomery's Cu-catalyzed borylative cyanation of allenes. [a] MeOH was used as additive. [b] standard procedure used then NaOH/H 2 O 2 ,overall yield shown for cyanodiboration and oxidation to the diol. Scheme 14. Cu-catalyzed borylation/ortho-cyanation reported by Buchwald and by Montgomery.Yields in parentheses are crude yields. Scheme 15. Yang and Liu's computational study of the Cu-catalyzed regioselective borylation/ortho-cyanation of vinylarenes. M = Cu or Li. Scheme 16. Yang's Cu-catalyzed 1,3-allyl group transfer borylation/ ortho-cyanation cascade.

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Section: Allenesmentioning

confidence: 99%

Copper‐Catalyzed Borylative Couplings with C−N Electrophiles

et al. 2020

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“…[31] The attractive advantageo ft his strategy was that the reaction proceeded througha na romatization-driven, copper-promoted rearrangement pathway. Proposed mechanism of the cobalt(III)-catalyzed CÀHc yanation reaction.…”

Section: Copper-catalyzed Electrophilic Cyanationmentioning

confidence: 99%

“…Ac opper-catalyzed borylation/ortho-cyanation/allyl-transfer cascade reaction was developed by the Yang group by using NCTS as ac yanating reagent (Scheme 25). [31] The attractive advantageo ft his strategy was that the reaction proceeded througha na romatization-driven, copper-promoted rearrangement pathway. Goodf unctional-group tolerance wasa lso observed in this reaction, thereby providing the cyanatedp roducts in good yields.…”

Section: Copper-catalyzed Electrophilic Cyanationmentioning

confidence: 99%

Transition‐Metal‐Catalyzed Cyanation by Using an Electrophilic Cyanating Agent, N‐Cyano‐N‐phenyl‐p‐toluenesulfonamide (NCTS)

Cui

Song

Liu

et al. 2018

Chemistry An Asian Journal

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The ability to introduce a nitrile group into a biologically active compound is very useful in organic synthesis, owing to the importance of nitrile groups in transformations and tuning molecular properties. To date, nucleophilic cyanation has been the most used strategy for this purpose, whilst electrophilic cyanation reactions are less developed. Recently, the electrophilic cyanation reagent N-cyano-N-phenyl-p-toluenesulfonamide (NCTS) has received increasing attention, owing to its superior properties in terms of safety and practicality. This Focus Review summarizes recent progress in transition-metal-catalyzed cyanation reactions that use NCTS.

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“…More recently, Yang applied NCTS for cyanation of 1-allyl-2-vinylnaphthalenes 127 under copper catalysis ( Scheme 24 d) [ 61 ]. Similar to previous work, this reaction cascade was initiated by a copper catalyzed electrophilic dearomatization process.…”

Section: Synthetic Applications Of Substituted Cyanamidesmentioning

confidence: 99%