The Non‐directed Distal
            <scp>C</scp>
            (sp
            <sup>2</sup>
            )–
            <scp>H</scp>
            Functionalization of Arenes

Mondal, Arup; Wedi, Philipp; Gemmeren, Manuel van

doi:10.1002/9783527824137.ch7

Cited by 4 publications

(3 citation statements)

References 193 publications

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“…Next to iridium and rhodium, which have been applied to the formation of C–B and C–Si bonds, palladium shows promise for versatile, nondirected functionalizations of C(sp 2 )–H bonds and enables direct formation of C–C bonds. 13 14 15 16 17 18 However, catalyst activity, control over regioselectivity, and application to complex molecules remain challenging. Heteroarenes and electron-rich or fluoro-substituted arenes can be utilized for palladium-catalyzed nondirected C–H functionalization, with the electronically and sterically differentiated C–H sites, and in certain cases even catalyst structure, governing the reactivity and site selectivity.…”

Section: C–h Activation and The Cmd Mechanismmentioning

confidence: 99%

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Introduction to Spatial Anion Control for Direct C–H Arylation

Čorić¹,

Dhankhar²

2022

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C–H activation of functionally rich molecules without the need for directing groups promises shorter organic syntheses and late-stage diversification of molecules for drug discovery. We highlight recent examples of palladium-catalyzed nondirected functionalization of C–H bonds in arenes as limiting substrates with a focus on the development of the concept of spatial anion control for direct C–H arylation.1 C–H Activation and the CMD Mechanism2 Nondirected C–H Functionalizations of Arenes as Limiting Substrates3 Nondirected C–H Arylation4 Spatial Anion Control for Direct C–H Arylation5 Coordination Chemistry with Spatial Anion Control6 Conclusion

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Section: C–h Activation and The Cmd Mechanismmentioning

confidence: 99%

“…22 50 51 In this section, we describe recent developments of palladium catalysts for direct C–H activation of arenes as limiting reactants for the formation of C–C bonds. 14 15…”

Section: Nondirected C–h Functionalization Of Arenes As Limiting Substratesmentioning

confidence: 99%

Introduction to Spatial Anion Control for Direct C–H Arylation

Čorić¹,

Dhankhar²

2022

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“…Such methods can be enabled through various mechanistic approaches, ranging from modern methods for electrophilic aromatic substitution, through radical-based methods (which can, for example, also be photoredox catalyzed or based on electrochemistry), to transition metal-enabled C–H activation processes. 1 4…”

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confidence: 99%

Dual Ligand-Enabled Late-Stage Fujiwara–Moritani Reactions

Santiago¹,

Chen²,

Mondal³

et al. 2021

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In this study, we describe the use of dual ligand-based palladium catalysts for the late-stage olefination of arenes. Building upon a method previously developed for simple arenes, a variety of complex arene substrates were functionalized. Importantly, the method uses the arene as a limiting reactant and is therefore suitable for valuable starting materials that cannot be used in excess. The regioselectivity of the transformation is controlled by the steric and electronic properties of the substrate, providing access to regioisomers that would be challenging to prepare through other synthetic approaches.

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Palladium-Catalyzed Nondirected Late-Stage C–H Deuteration of Arenes

et al. 2021

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We describe a palladium-catalyzed nondirected late-stage deuteration of arenes. Key aspects include the use of D2O as a convenient and easily available deuterium source and the discovery of highly active N,N-bidentate ligands containing an N-acylsulfonamide group. The reported protocol enables high degrees of deuterium incorporation via a reversible C–H activation step and features extraordinary functional group tolerance, allowing for the deuteration of complex substrates. This is exemplified by the late-stage isotopic labeling of various pharmaceutically relevant motifs and related scaffolds. We expect that this method, among other applications, will prove useful as a tool in drug development processes and for mechanistic studies.

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The Non‐directed Distal C (sp ² )– H Functionalization of Arenes

Cited by 4 publications

References 193 publications

Introduction to Spatial Anion Control for Direct C–H Arylation

Introduction to Spatial Anion Control for Direct C–H Arylation

Dual Ligand-Enabled Late-Stage Fujiwara–Moritani Reactions

Palladium-Catalyzed Nondirected Late-Stage C–H Deuteration of Arenes

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The Non‐directed Distal C (sp 2 )– H Functionalization of Arenes

Cited by 4 publications

References 193 publications

Introduction to Spatial Anion Control for Direct C–H Arylation

Introduction to Spatial Anion Control for Direct C–H Arylation

Dual Ligand-Enabled Late-Stage Fujiwara–Moritani Reactions

Palladium-Catalyzed Nondirected Late-Stage C–H Deuteration of Arenes

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Product

Resources

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The Non‐directed Distal C (sp ² )– H Functionalization of Arenes