790-22-7

Upstream product

• 16170-82-4 [14C]methyl iodide 
• 101-81-5 Diphenylmethane 
• 92-52-4 biphenyl 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 71-43-2 benzene 
• 1016160-90-9 3-(methoxymethyl)-1,1'-biphenyl 
• 823-78-9 meta-bromobenzyl bromide 
• 98-80-6 phenylboronic acid 
• 14704-31-5 3-(bromomethyl)-1,1'-biphenyl 
• 16635-23-7 phenyltriisopropoxytitanium(IV) 
• 69605-90-9 3-phenyl-benzyl alcohol 
• 38580-82-4 3-biphenylylmethyl chloride 
• 5123-13-7 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane 

Relevant academic research and scientific papers

Cu-Catalyzed Suzuki-Miyaura reactions of primary and secondary benzyl halides with arylboronates

A copper-catalyzed Suzuki-Miyaura coupling of benzyl halides with arylboronates is described. Varieties of primary benzyl halides as well as more challenging secondary benzyl halides with β hydrogens or steric hindrance could be successfully converted into the corresponding products. Thus it provides access to diarylmethanes, diarylethanes and triarylmethanes. This journal is the Partner Organisations 2014.

Extremely efficient cross-coupling of benzylic halides with aryltitanium tris(isopropoxide) catalyzed by low loadings of a simple palladium(II) acctate/Tris(p-tolyl)phosphine system

Highly efficient coupling reactions of benzylic bromides or chlorides with aryltitanium tris(isopropoxide) [ArTi(O-i-Pr)3] catalyzed by a simple palladium(II) Acctate/tris(p-tolyl)phosphine [Pd(OAc)2/ P(p-tolyl)3] system are reported. The coupling reactions proceed in general at room temperature employing low catalyst loadings of 0.02 to 0.2 mol%, affording coupling products in excellent yields of up to 99%. For benzylic bromides bearing strong electronwithdrawing cyano (CN) or trifluoromethyl (CF 3) substituents, the reactions require a higher catalyst loading of 1 mol%, or the reactions are carried out at 60°C. The catalytic system also tolerates (1-bromoethyl)benzene bearing β-hydrogen atoms while using a catalyst loading of 1 mol% to afford the coupling product in a 70% yield.

Dichloro-bis(aminophosphine) complexes of palladium: Highly convenient, reliable and extremely active suzuki-miyaura catalysts with excellent functional group tolerance

Dichloro-bis(aminophosphine) complexes are stable depot forms of palladium nanoparticles and have proved to be excellent SuzukiMiyaura catalysts. Simple modifications of the ligand (and/or the addition of water to the reaction mixture) have allowed their formation to be controlled. Dichlorobis[1- (dicyclohexylphosphany1)piperidine]palladium (3), the most active catalyst of the investigated systems, is a highly convenient, reliable, and extremely active Suzuki catalyst with excellent functional group tolerance that enables the quantitative coupling of a wide variety of activated, nonactivated, and deactivated and/or sterically hindered functionalized and heterocyclic aryl and benzyl bromides with only a slight excess (1.1-1.2 equiv) of arylboronic acid at 80°C in the presence of 0.2 mol % of the catalyst in technical grade toluene in flasks open to the air. Conversions of >95% were generally achieved within only a few minutes. The reaction protocol presented herein is universally applicable. Side-products have only rarely been detected. The catalytic activities of the aminophosphine-based systems were found to be dramatically improved compared with their phosphine analogue as a result of significantly faster palladium nanoparticle formation. The decomposition products of the catalysts are dicyclohexylphosphinate, cyclohexylphosphonate, and phosphate, which can easily be separated from the coupling products, a great advantage when compared with non-water-soluble phosphine-based systems.

Benzylation of arenes through FeCl3-catalyzed Friedel-Crafts reaction via C-O activation of benzyl ether

Various benzyl ethers were converted to benzyl arenes via a FeCl3-catalyzed Friedel-Crafts alkylation reaction under mild condition in good yields. This method also offered a simple and practical approach to synthesize di- or tri-aryl methanes and aryl heteroaryl methanes through the activation of C-O bonds.

Synthesis of 4-alkyl-4-(4-methoxyphenyl)cyclohex-2-en-1-ones and 5-alkyl-5-phenyl-1,3-cyclohexadienes from bis(tricarbonylchromium)-coordinated biphenyls

(η6:η6-Biphenyl)[Cr(CO)3] 2 and (η6η64,4'-dimethoxybiphenyl) [Cr(CO)3]2 were chemically reduced with lithium anthracenide or lithium naphthalenide in THF to generate s