Pd(II)-Catalyzed C−H Activation/Aryl−Aryl Coupling of Phenol Esters

Xiao, Bin; Fu, Yao; Xu, Jun; Gong, Tian‐Jun; Dai, Jianjun; Yi, Jun; Liu, Lei

doi:10.1021/ja909818n

Cited by 359 publications

(126 citation statements)

References 42 publications

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“…[1] or more recently Ar À O group (e.g., phenol esters, phenoxypyridines)]. [2] To overcome the first issue a small number of examples of removable and modifiable Si-, B-and Nbased directing groups have been recently reported, [3,4] however, the identification of new detachabale and/or modifiable directing agents would be very valuable for further synthetic applications. On the other hand, the introduction of S-containing directing groups is very desirable due to the importance of sulfur derivatives in nature (e.g., cysteine-cystine couple, etc.…”

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confidence: 99%

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Modifiable Sulfur Tethers as Directing Groups for Aromatic CH Acetoxylation Reactions

2011

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A designed new class of modifiable sulfur tethers for aromatic C À H bond functionalizations is presented. As a model, the palladium-catalyzed directed acetoxylation reaction was studied. The more challenging sulfoxide tethers were the most effective in this transformation, showing a broad functionality tolerance, high S oxido-redox stability and no catalyst poisoning. Preliminary mechanistic studies indicate that the higher reactivity and selectivity shown by the sulfoxide tethers vs. the corresponding sulfones can be attributed to an extra coordination of the sulfoxide S atom to the catalyst. The utility of the presented methodology to generate structurally interesting aromatic derivatives by a subsequent modification of the S-tether is also exemplified.Keywords: acetoxylation; arenes; C À H activation; sulfur; synthetic methodsIn the past few years, the development of metal-catalyzed ortho-directed C À H bond functionalizations of arenes [1] has experienced particular attention towards more atom efficient transformations. Although great advances in this area have been made, there are still some intrinsic limitations in this approach: i) the structural scope of the substrate due to the presence of the directing group at the end of the transformation, and ii) the nature of the employed directing groups [mainly restricted to Ar À C group (e.g

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confidence: 99%

“…[a] 1 (0.15 mmol), PdA C H T U N G T R E N N U N G (OAc) 2 and oxidant in 1:1 DCE:AcOH (1 mL). [b] Isolated yield.…”

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confidence: 99%

Modifiable Sulfur Tethers as Directing Groups for Aromatic CH Acetoxylation Reactions

2011

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“…11 In this field, a variety of removable directing groups have been developed for the activation of Csp 2 -H bonds; for instance, N-acyl, 12 O-acyl, 13 N-carbamoyl, 14 Ocarbamoyl, 15 carboxylic, 16 and N-oxides. 17 Due to the importance of the indole unit in pharmaceuticals and bioactive compounds, as a first process, we focused our attention on the Pd-catalyzed regioselective C-2 alkenylation indoles.…”

Section: Methodsmentioning

confidence: 99%

Coordinating Sulfonyl Substrates in Metal-Catalyzed Reactions

Hernández

Rubia

Urones

et al. 2011

Phosphorus, Sulfur, and Silicon and the Related Elements

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Metal-coordinating heteroaryl sulfonyl groups, such as the 2-pyridylsulfonyl and the 8-quinolylsulfonyl group, allow the control of the reactivity and stereoselectivity of a great variety of metal-mediated reactions. This concept is rather general and has been applied for the activation of vinyl sulfones and N-sulfonyl imines, as well as in the direct C H functionalization of N-H heterocycles. In particular, this kind of coordinating group has played a key role in the enantioselective Rh-catalyzed addition of boronic acids and Cu-catalyzed reduction of 2-pyridyl vinyl sulfones, the Cu-catalyzed addition of organozinc reagents, and the direct Mannich reaction of glycinate imines to N-heteroarylsulfonyl imines. In addition, a general procedure for the Pd-catalyzed C-2 alkenylation of N-(2-pyridylsulfonyl)indoles and pyrroles has been developed.

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“…101 In most cases the pure arylated esters (143) have been prepared in good to excellent yields. Interestingly, during the reaction process certain substrates controllably provided the free phenol products (144).…”

Section: Synlett Letter / Cluster / New Toolsmentioning

confidence: 99%

Diaryliodonium Salts in Organic Syntheses: A Useful Compound Class for Novel Arylation Strategies

Aradi

Tóth

Tolnai

et al. 2016

Synlett

188

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This account aims to give a description of the usefulness of diaryliodonium salts in organic chemistry, including their synthesis and applications in the presence and absence of transition metal catalysts. Herein, we briefly summarize the structural properties and reactivity of diaryliodonium salts. We collected several applications of the hypervalent reagents including metal-free arylations of C, O, N and S nucleophiles. Synthesis and functionalization of aromatic and heteroaromatic systems via copper and palladium catalyzed transformations are also discussed in this account.

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Pd(II)-Catalyzed C−H Activation/Aryl−Aryl Coupling of Phenol Esters

Cited by 359 publications

References 42 publications

Modifiable Sulfur Tethers as Directing Groups for Aromatic CH Acetoxylation Reactions

Modifiable Sulfur Tethers as Directing Groups for Aromatic CH Acetoxylation Reactions

Coordinating Sulfonyl Substrates in Metal-Catalyzed Reactions

Diaryliodonium Salts in Organic Syntheses: A Useful Compound Class for Novel Arylation Strategies

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