Suzuki–Miyaura cross-coupling of amides and esters at room temperature: correlation with barriers to rotation around C–N and C–O bonds

Lei, Peng; Meng, Guangrong; Shi, Shicheng; Ling, Yun; An, Jie; Szostak, Roman; Szostak, Michal

doi:10.1039/c7sc02692g

Cited by 149 publications

(83 citation statements)

References 73 publications

(29 reference statements)

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“…Interestingly,i n2 017, Szostak and co-workersr eported a PdÀNHC-catalyzed Suzuki-Miyaura cross-coupling reaction of esters and amides with boron-based partnerst hrough NÀC and OÀCa ctivation,r espectively (Scheme 21). [56] Their elegant method used ab ench-stable, commerciallya vailable[ ( h 3 -1-tBuindenyl)Pd(IPr)(Cl)] catalyst. Ac orrelation between the relative reactivities of the amides was performed and the N-Ph,N-Boc amide was found to be the most-reactive amide for this transformation.…”

Section: Cross-coupling and Other Reactionsmentioning

confidence: 99%

Recent Advances in the Metal‐Catalyzed Activation of Amide Bonds

Chaudhari

Gnanaprakasam

2018

Chemistry An Asian Journal

122

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The amide functional group is commonly found in peptides, proteins, pharmaceutical compounds, natural products, andp olymers.T he synthesis of amides is typically performed by using classical approaches that involvet he reaction between ac arboxylic acid and an amine in the presence of an activator.Amides are thought to be an inert functional group, because they are unsusceptible to nucleophile attack, owing to their low electrophilicity.T he reason fort his resistancei sc lear:t he resonance stability of the amide bond. However,t ransition metal catalysis can circumvent this stability by selectively rupturing the NÀCb ond of the amide, thereby facilitating further cross-couplingo ro ther reactions.Inthis Focus Review,wediscuss the recent advances in this area and present as ummary of methods that have been developed for activating the amide NÀCb ond by using precious and non-preciousmetals.

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Section: Cross-coupling and Other Reactionsmentioning

confidence: 99%

Recent Advances in the Metal‐Catalyzed Activation of Amide Bonds

Chaudhari

Gnanaprakasam

2018

Chemistry An Asian Journal

122

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“…With this goal, three successive catalytic systemsw ere developedi nvolving in each case ap alladium/ NHC catalytic system. [58][59][60] With these catalytic systems, arylboronic acid can be used directly at moderate or even room temperature with aryl and aliphatic N-Boc-amides. The scope of these methodologies is broad allowing the coupling of aryl or even heteroaryl moieties (Scheme 16).…”

Section: Càc(sp 2 )B Ond-forming Reactionsmentioning

confidence: 99%

N‐Boc‐Amides in Cross‐Coupling Reactions

Bourne‐Branchu

Gosmini

Danoun

2018

Chemistry A European J

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Since 2015, the use of amides as electrophilic partners in cross‐coupling reactions has experienced exponential growth. Diverse amide derivatives have been studied and among them N‐Boc‐amides have shown good activities towards various cross‐coupling reactions and presents, in our view, an important synthetic usefulness. This review describes the recent developments of these chemical transformations involving N‐Boc‐amides.

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“…aryl halides) have spurred the efforts to develop practical methods for the cross-coupling of bench-stable acyl electrophiles. [6] To date, significant progress in the NÀ C(O) crosscoupling has been achieved using Pd(II)À NHC (NHC = N-heterocyclic carbene) precatalysts. [7] However, the use of phosphines as practical, cheap and readily available ancillary ligands remains a major challenge.…”

Section: Introductionmentioning

confidence: 99%

Suzuki‐Miyaura Cross‐Coupling of Amides using Well‐Defined, Air‐Stable [(PR₃)₂Pd(II)X₂] Precatalysts

Zhou

et al. 2020

Adv Synth Catal

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A versatile method for the Suzuki-Miyaura cross-coupling of amides using highly active, welldefined, and air-stable PdÀ phosphine precatalysts is reported. Most notably, the method represents the first example of using practical and operationally-simple Pd(II)À phosphine precatalysts in the emerging amide bond cross-coupling manifold. The reactions are efficient at 0.10 mol% loading, furnishing biaryl ketones with high chemoselectivity for NÀ C(O) bond cleavage. This versatile method enables for the first time to achieve PdÀ phosphine-catalyzed cross-coupling of amides at ppm loading. This CÀ N cross-coupling can be used to efficiently furnish pharmaceutical intermediates by orthogonal Pd-catalyzed cross-couplings. We fully expect that operationally-simple [(PR 3 ) 2 Pd(II)X 2 ] precatalysts as effective triggers for NÀ C(O) cross-coupling will be of broad synthetic and catalytic interest.

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Suzuki–Miyaura cross-coupling of amides and esters at room temperature: correlation with barriers to rotation around C–N and C–O bonds

Abstract: We report the first general palladium-catalyzed Suzuki–Miyaura cross-coupling of both common amides and aryl esters through the selective cleavage of the C–N and C–O bonds at ambient temperature.

Cited by 149 publications

References 73 publications

Recent Advances in the Metal‐Catalyzed Activation of Amide Bonds

Recent Advances in the Metal‐Catalyzed Activation of Amide Bonds

N‐Boc‐Amides in Cross‐Coupling Reactions

Suzuki‐Miyaura Cross‐Coupling of Amides using Well‐Defined, Air‐Stable [(PR₃)₂Pd(II)X₂] Precatalysts

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Suzuki–Miyaura cross-coupling of amides and esters at room temperature: correlation with barriers to rotation around C–N and C–O bonds

Abstract: We report the first general palladium-catalyzed Suzuki–Miyaura cross-coupling of both common amides and aryl esters through the selective cleavage of the C–N and C–O bonds at ambient temperature.

Cited by 149 publications

References 73 publications

Recent Advances in the Metal‐Catalyzed Activation of Amide Bonds

Recent Advances in the Metal‐Catalyzed Activation of Amide Bonds

N‐Boc‐Amides in Cross‐Coupling Reactions

Suzuki‐Miyaura Cross‐Coupling of Amides using Well‐Defined, Air‐Stable [(PR3)2Pd(II)X2] Precatalysts

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Suzuki‐Miyaura Cross‐Coupling of Amides using Well‐Defined, Air‐Stable [(PR₃)₂Pd(II)X₂] Precatalysts