35065-86-2

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 48, p. 1542, 1983 DOI: 10.1021/jo00157a035

InChI:InChI=1/C8H7BrO2/c1-6(10)11-8-4-2-3-7(9)5-8/h2-5H,1H3

Upstream product

• 93-59-4 Perbenzoic acid 
• 67-66-3 chloroform 
• 2142-63-4 1-(3-Bromophenyl)ethanone 
• 45634-03-5 3-Bromo-phenol anion 
• 830-03-5 4-nitrophenol acetate 
• 591-20-8 3-Bromophenol 
• 75-36-5 acetyl chloride 
• 108-22-5 Isopropenyl acetate 
• 135715-84-3 4-(5-fluoro-3-mercaptophenyl)-4-methoxytetrahydropyran 
• 161386-22-7 4'-[5-fluoro-3-(4-methoxytetrahydropyran-4-yl)phenylthio]-2'-methoxyacetophenone 
• 7664-93-9 sulfuric acid 
• 89368-12-7 1-[4-bromo-2-(methyloxy)phenyl]ethanone 
• 108-86-1 bromobenzene 
• 3240-34-4 [bis(acetoxy)iodo]benzene 

Downstream Products

• 591-20-8 3-Bromophenol 
• 30186-18-6 4'-bromo-2'-hydroxyacetophenone 
• 61791-99-9 2-bromo-4-hydroxyacetophenone 
• 2466-76-4 N-Acetylimidazole 
• 45634-03-5 3-Bromo-phenol anion 
• 55736-69-1 1-(2-bromo-6-hydroxyphenyl)ethan-1-one 
• 1215212-06-8 C₁₅H₁₃FO₃ 
• 1465766-23-7 C₅₃H₅₂O₁₀ 
• 1465766-26-0 C₅₅H₅₆O₁₀ 
• 1465766-28-2 C₅₃H₅₂O₁₀ 
• 1465766-29-3 C₅₈H₆₂O₁₀ 
• 1465766-32-8 C₅₅H₅₆O₁₀ 
• 1465766-34-0 C₅₈H₆₂O₁₀ 
• 1465766-36-2 C₅₀H₄₆O₁₀ 

Relevant academic research and scientific papers

Steric effect of NHC ligands in Pd(II)–NHC-catalyzed non-directed C–H acetoxylation of simple arenes

Although there has been a lot of progress in oxidative arene C–H functionalization reactions catalyzed by Pd(II/IV) system, the non-directed, site-selective functionalization of arene molecules is still challenging. It has been established that ligands play a pivotal role in controlling rate- as well as selectivity-determining step in a catalytic cycle involving well-defined metal-ligand bonding. N-heterocyclic carbene (NHC) ligands have had a tremendous contribution in the recent extraordinary success of achieving high reactivity and excellent selectivity in many catalytic processes including cross-coupling and olefin-metathesis reactions. However, the immense potential of these NHC ligands in improving site-selectivity of non-directed catalytic C–H functionalization reactions of simple arenes is yet to be realized, where overriding the electronic bias on deciding selectivity is a burdensome task. The presented work demonstrated an initiative step in this regard. Herein, a series of well-defined discrete [Pd(NHCR′R)(py)I2] complexes with systematically varied degree of spatial congestion at the Pd centre, exerted through the R and R’ substituents on the NHC ligand, were explored in controlling the activity as well as the site-selectivity of non-directed acetoxylation of representative monosubstituted and disubstituted simple arenes (such as toluene, iodobenzene and bromobenzene, naphthalene and 1,2-dichlorobenzene). The resulting best yields were found to be 75% for toluene and 65% for bromobenzene with [Pd(NHCMePh)(py)I2], 75% for iodobenzene and 79% for naphthalene with [Pd(NHCMeMe)(py)I2], and 41% for 1,2-dichlorobenzene with [Pd(NHCCyCy)(py)I2]. Most importantly, with increasing the bulkiness of the NHC ligand in the complexes, the selectivity of the distal C-acetoxylated products in comparison to the proximal ones, was enhanced to a great extent in all cases. Considering the vast library of NHC ligands, this study underscores the future opportunity to develop more strategies to improve the activity and the crucial site-selectivity of C–H functionalization reactions in simple as well as complex organic molecules.

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