Palladium(II)‐Catalyzed <i>ortho</i>‐Arylation of Aromatic Alcohols with a Readily Attachable and Cleavable Molecular Scaffold

Li, Qiankun; Knight, Brian J.; Ferreira, E.

doi:10.1002/chem.201602844

Cited by 10 publications

(6 citation statements)

References 52 publications

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“…Moreover, the synthetic potential of this PyA auxiliary was further highlighted by the fact that it could be installed in a one-pot process, followed by C−H alkenylation, and could then be removed to afford the corresponding alkenylated arene alcohol 309 in good yield with the directing group being recovered in high yield (Scheme 144b). Using a similar N,O-based directing group that contains a quinoline-based acetal (QuA), Ferreira subsequently reported the Pd-catalyzed ortho-arylation of the benzyl alcohol derivative 310 with arylboron reagents (Scheme 145a) 578 and the meta-arylation of the benzyl alcohol derivative 312 with aryl iodides in combination with a Pd/ norbornene-CO 2 Me catalytic system (Scheme 145b). 579 In 2017, Lupton and Maiti reported the Pd-catalyzed metaselective C(sp 2 )−H bond alkenylation with activated alkenes aided by an 8-nitroquinoline-or 8-methoxyquinoline-based directing groups (Scheme 146).…”

Section: Arylation and Alkynylation Continuous Efforts Bymentioning

confidence: 99%

Bidentate Directing Groups: An Efficient Tool in C–H Bond Functionalization Chemistry for the Expedient Construction of C–C Bonds

2020

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During the past decades, synthetic organic chemistry discovered that directing group assisted C−H activation is a key tool for the expedient and siteselective construction of C−C bonds. Among the various directing group strategies, bidentate directing groups are now recognized as one of the most efficient devices for the selective functionalization of certain positions due to fact that its metal center permits fine, tunable, and reversible coordination. The family of bidentate directing groups permit various types of assistance to be achieved, such as N,N-dentate, N,O-dentate, and N,S-dentate auxiliaries, which are categorized based on the coordination site. In this review, we broadly discuss various C− H bond functionalization reactions for the formation of C−C bonds with the aid of bidentate directing groups.

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Section: Arylation and Alkynylation Continuous Efforts Bymentioning

confidence: 99%

Bidentate Directing Groups: An Efficient Tool in C–H Bond Functionalization Chemistry for the Expedient Construction of C–C Bonds

2020

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“…98 Here, a cocktail of acetates containing LiOAc$2H 2 O, CsOAc, as well as Cu(OAc) 2 $H 2 O, and AsPh 3 as the optimal ligand were found to be crucial to obtain satisfactory product yields. The powerful palladium(II)/norbornene-catalyzed meta-selective C-H activation process could be further extended to benzylsulfonamides 99 and benzylic alcohols 100 by Yu and co-workers and Ferreira and coworkers, respectively.…”

Section: C-h Functionalization With Norbornene Mediatormentioning

confidence: 99%

Transient Directing Groups for Transformative C–H Activation by Synergistic Metal Catalysis

Gandeepan

Ackermann

2018

Chem

548

200

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The development of methods for the functionalization of otherwise inert C-H bonds is one of the major foci in molecular syntheses. Recent advances have significantly improved the arsenal of synthetic chemistry, enabling the use of less functionalized starting materials, a reduction of energy consumption, and a minimization of waste production. Despite undisputable progress, the main challenge associated with synthetically meaningful C-H activations is achieving positional selectivity. Thus far, the most common approach to address site selectivity in transition-metal-catalyzed intermolecular transformations is constituted by chelation assistance through directing groups. The installation and removal of these directing groups adds additional steps, compromising the step-economical nature of the overall C-H activation strategy. In contrast, here we discuss the emergence of transient directing group approaches through the in situ installation and deconstruction of a Lewis-basic entity with the aid of co-catalytic additives for selective C-H functionalizations.

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“…A sequential procedure of arylation with immediate subsequent scaffold cleavage afforded biaryl alcohol 6 an in 83 % yield . Methyl acetal‐derived scaffold (QuAOMe, 7 ) was also recovered in 94 % yield; we have shown that this compound can be reused in further attachment sequences . Furthermore, a telescoping procedure for this meta ‐arylation process using our quinolinyl scaffold could also be performed.…”

Section: Figurementioning

confidence: 96%

Meta‐Selective C−H Arylation of Aromatic Alcohols with a Readily Attachable and Cleavable Molecular Scaffold

Ferreira

2017

Chemistry A European J

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The first example of meta-selective C–H arylations of arene alcohol-based substrates is described. The strategy involves the combination of the transient norbornene strategy with the quinoline-based acetal scaffold to achieve the formation of biaryl compounds. Both a two-step meta-arylation/scaffold cleavage process and a total telescoping procedure are described, highlighting the convenient attributes of attachment, removal, and recovery of the acetal scaffold. Moreover, the meta-arylated compounds can be further derivatized via ortho-selective functionalizations. These processes establish a foundation for catalytic polyfunctionalization of alcohol-based compounds.

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Palladium(II)‐Catalyzed ortho‐Arylation of Aromatic Alcohols with a Readily Attachable and Cleavable Molecular Scaffold

Cited by 10 publications

References 52 publications

Bidentate Directing Groups: An Efficient Tool in C–H Bond Functionalization Chemistry for the Expedient Construction of C–C Bonds

Bidentate Directing Groups: An Efficient Tool in C–H Bond Functionalization Chemistry for the Expedient Construction of C–C Bonds

Transient Directing Groups for Transformative C–H Activation by Synergistic Metal Catalysis

Meta‐Selective C−H Arylation of Aromatic Alcohols with a Readily Attachable and Cleavable Molecular Scaffold

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