A Highly <i>Para</i>‐Selective Copper(II)‐Catalyzed Direct Arylation of Aniline and Phenol Derivatives

Ciana, Claire-Lise; Phipps, Robert J.; Brandt, Jochen R.; Meyer, Falco-Magnus; Gaunt, Matthew J.

doi:10.1002/anie.201004703

Cited by 330 publications

(111 citation statements)

References 55 publications

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“…In same year Ciana et al disclosed Friedel-Craft-type Cu-catalyzed paraselective arylation of electron rich phenol ethers alongwith secondary and tert-anilines with diaryliodonium salts (Schemes 49 and 50) (87). Excellent selectivity with good yield was observed for various oxygen bearing arenes and different diaryliodonium salts (Scheme 49).…”

Section: Para C-h Activationmentioning

confidence: 96%

“…Various functional groups were well tolerated on both coupling partners with moderate to good yield. Although excess of Pd(OAc) 2 (20 mol%) and PPh 3 (40 mol%) were used but this was first examples for the synthesis of selective 4-arylated phenols with wide substrate scope (87). aqueous media and various coordinating group such as amides, acids, as well as ketones were well tolerated at aryl iodide.…”

Section: Para C-h Activationmentioning

confidence: 99%

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Distant C-H Activation/Functionalization: A New Horizon of Selectivity Beyond Proximity

et al. 2015

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Activation/functionalization of inert C-H bond has undergone rapid growth in last decade and provides novel retro-synthetic disconnections for the synthesis of valuable molecules. The selectivity is often achieved by the use of directing group and is mainly limited to the proximal C-H bond. Initially, meta C-H activations were based on electronic or steric control and now it can be achieved by employing nitrile-based end-on-template as the directing group. The compilation of the remote C-H activation strategy will provide the useful linkage to the scientific community. This article is focused on recent progress in remote C-H activation, mechanistic understanding, and its applications in the field of total synthesis of targeted molecules.

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Section: Para C-h Activationmentioning

confidence: 96%

Section: Para C-h Activationmentioning

confidence: 99%

Distant C-H Activation/Functionalization: A New Horizon of Selectivity Beyond Proximity

et al. 2015

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“…Additionally notable is the high para-selectivity when a similar Cu/diaryliodonium salt system is applied to the direct arylation of anisoles and anilines (Scheme 10). 13 …”

Section: C-h/c-x Couplingmentioning

confidence: 99%

Recent Advances in Copper-mediated Direct Biaryl Coupling

2015

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Copper salts and complexes have recently received significant attention as less expensive, abundant, and unique alternatives to noble transition-metal catalysts such as palladium, rhodium, and ruthenium, in the research field of C–H activation. This highlight review focuses on recent advances in copper-mediated biaryl coupling via aromatic C–H cleavage, and the scope and limitations are briefly summarized.

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“…Diaryliodonium salts have recently been recognized as versatile reagents in organic synthesis. 2 They can be employed both in metal mediated and metal-free reactions thereby avoiding the potential drawbacks of organometallic chemistry such as toxicity and high cost. 3 Efficient one-pot procedures to diaryliodonium salts have been developed within our group (Scheme 1) increasing the availability of these compounds.…”

Section: Introductionmentioning

confidence: 99%