ChemInform Abstract: Directed meta‐Selective Bromination of Arenes with Ruthenium Catalysts.

Yu, Qingzhen; Hu, Liming; Wang, Yue; Zheng, Shasha; Huang, Jianhui

doi:10.1002/chin.201616044

Cited by 5 publications

(9 citation statements)

References 18 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Thus, chelation assistance has proven particularly instrumental for proximity-induced ortho -C–H functionalizations 16 17 18 19 . In stark contrast, remote arene functionalizations continue to be challenging, with major recent progress being achieved by inter alia complementary palladium 20 21 22 23 24 25 26 27 28 29 , iridium 30 31 , rhodium 32 and ruthenium 33 34 35 36 37 38 39 catalysis through steric control, template assistance, weak hydrogen bonding, transient mediators or catalytic σ-activation by ortho -C–H metalation ( Fig. 1a ) 40 .…”

mentioning

confidence: 99%

“…Despite undisputable advances, these methods typically offer access to only a single compound class. Furthermore, all protocols for ruthenium-catalysed meta -C–H functionalization 33 34 35 36 37 38 39 continue to be restricted to nitrogen-containing heterocycles, such as 2-arylpyridines, as the directing group. Since such heteroarenes are difficult to modify or remove 39 41 , the synthetic utility of this strategy is significantly compromised.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Ruthenium(II)-catalysed remote C–H alkylations as a versatile platform to meta-decorated arenes

et al. 2017

View full text Add to dashboard Cite

The full control of positional selectivity is of prime importance in C–H activation technology. Chelation assistance served as the stimulus for the development of a plethora of ortho-selective arene functionalizations. In sharp contrast, meta-selective C–H functionalizations continue to be scarce, with all ruthenium-catalysed transformations currently requiring difficult to remove or modify nitrogen-containing heterocycles. Herein, we describe a unifying concept to access a wealth of meta-decorated arenes by a unique arene ligand effect in proximity-induced ruthenium(II) C–H activation catalysis. The transformative nature of our strategy is mirrored by providing a step-economical entry to a range of meta-substituted arenes, including ketones, acids, amines and phenols—key structural motifs in crop protection, material sciences, medicinal chemistry and pharmaceutical industries.

show abstract

mentioning

confidence: 99%

mentioning

confidence: 99%

Ruthenium(II)-catalysed remote C–H alkylations as a versatile platform to meta-decorated arenes

et al. 2017

View full text Add to dashboard Cite

show abstract

“…267 Pyridine and pyrazine directing groups were most effective, whereas pyrazoles and quinolines only afforded the desired products in low yield. The authors also showed that the reaction is completely inhibited in the presence of excess BHT, suggesting that the mechanism for this bromination may involve radical intermediates.…”

Section: Ru-and W-catalyzed Synthesis Of Aryl Halidesmentioning

confidence: 99%

Modern Transition-Metal-Catalyzed Carbon–Halogen Bond Formation

2016

View full text Add to dashboard Cite

The high utility of halogenated organic compounds has prompted the development of a vast number of transformations which install the carbon-halogen motif. Traditional routes to these building blocks have commonly involved multiple steps, harsh reaction conditions, and the use of stoichiometric and/or toxic reagents. In this regard, using transition metals to catalyze the synthesis of organohalides has become a mature field in itself, and applying these technologies has allowed for a decrease in the production of waste, higher levels of regio- and stereoselectivity, and the ability to produce enantioenriched target compounds. Furthermore, transition metals offer the distinct advantage of possessing a diverse spectrum of mechanistic possibilities which translate to the capability to apply new substrate classes and afford novel and difficult-to-access structures. This Review provides comprehensive coverage of modern transition metal-catalyzed syntheses of organohalides via a diverse array of mechanisms. Attention is given to the seminal stoichiometric organometallic studies which led to the corresponding catalytic processes being realized. By breaking this field down into the synthesis of aryl, vinyl, and alkyl halides, it becomes clear which methods have surfaced as most favored for each individual class. In general, a pronounced shift toward the use of C-H bonds as key functional groups, in addition to methods which proceed by catalytic, radical-based mechanisms has occurred. Although always evolving, this field appears to be heading in the direction of using starting materials with a significantly lower degree of prefunctionalization in addition to less expensive and abundant metal catalysts.

show abstract

“…Initially, we used the hydrocinnamic amide 1a' (Table 1) bearing an aryl carboxyl meta-directing template as the substrate to investigate the C-H iodination using an aryl iodide, since desired meta-C-H iodinated product had been obtained as a side product with 1a' in our previous study. 61 Moreover, meta-C-H iodination [70][71][72] of arenes is still very limited to narrow substrate scope, [90][91][92][93][94][95][96][97][98][99][100][101][102][103][104][105][106][107] and hydrocinnamic acids are a class of important core structure of biologically active molecules such as drug Baclofen.…”

Section: C-h Arylation Only Via C-c Rementioning

confidence: 99%

Arene C–H Iodination Using Aryl Iodides

Zhang

et al. 2022

CCS Chem

View full text Add to dashboard Cite

C-H metathesis reaction is extremely rare. Herein we report the first Pd(II)-catalyzed C-H iodination of arenes using 2-nitrophenyl iodides as the mild iodinating reagents via a formal metathesis reaction.Unusual C-I bond formation occurred in preference to competing C-C coupling in this reaction with aryl iodides. Assisted by aliphatic carboxyl directing groups, a range of hydrocinnamic acids and related arenes could be selectively iodinated at either meta-or ortho-positions of the phenyl ring. Remote diastereoselective C-H activation was also promising. This method may open up a new way to iodinate challenging substrates.

show abstract

ChemInform Abstract: Directed meta‐Selective Bromination of Arenes with Ruthenium Catalysts.

Cited by 5 publications

References 18 publications

Ruthenium(II)-catalysed remote C–H alkylations as a versatile platform to meta-decorated arenes

Ruthenium(II)-catalysed remote C–H alkylations as a versatile platform to meta-decorated arenes

Modern Transition-Metal-Catalyzed Carbon–Halogen Bond Formation

Arene C–H Iodination Using Aryl Iodides

Contact Info

Product

Resources

About