790-22-7

Upstream product

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

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.

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.

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.

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