502483-86-5

Upstream product

• 478176-03-3 1-[(2E,4)-pentadienyloxy]-3-phenyl-2-propyne 
• 14371-10-9 (E)-3-phenylpropenal 
• 50402-81-8 biphenyl-2,3-dicarboxylic acid dimethyl ester 
• 16939-57-4 (E)-buta-1,3-dienylbenzene 
• 53877-63-7 (3-(prop-2-ynyloxy)prop-1-ynyl)benzene 
• 1066-54-2 trimethylsilylacetylene 
• 127168-82-5 3-bromo-1,2-bis(bromomethyl)benzene 
• 576-23-8 2,3-dimethylbromobenzene 
• 1402667-16-6 4-bromo-1,3-dihydroisobenzofuran 
• 98-80-6 phenylboronic acid 

Downstream Products

• 76350-90-8 (2-methyl-[1,1′-biphenyl]-3-yl)methanol 
• 1028202-48-3 2-[3-(hydroxymethyl)biphenyl-2-yl]-1-phenylethanol 

Relevant academic research and scientific papers

Intramolecular [2+2+1] cycloadditions with (cyclobutadiene)tricarbonyliron

(Chemical Equation Presented) Highly functionalized strained rings are prepared through the cycloaddition of cyclobutadiene to alkynes. An intramolecular [2+2+1] cycloaddition is optimized for a variety of (cyclobutadiene)tricarbonyliron substrates with t

Iridium complex-catalyzed enantioselective intramolecular [4+2] cycloaddition of dieneynes

A catalytic and highly enantioselective intramolecular [4+2] cycloaddition of dieneynes was achieved by use of chiral iridium complex prepared in situ from [IrCl(cod)]2 and BDPP [2,4-bis(diphenylphosphino)pentane]. The reaction proceeded in refluxed tert-butyl acetate to give chiral cyclohexa-1,4-dienes in very high enantiomeric excess.

Highly-functionalized arene synthesis based on palladium on carbon-catalyzed aqueous dehydrogenation of cyclohexadienes and cyclohexenes

Transition metal-catalyzed dehydrogenation is a clean oxidation method requiring no additional oxidants. We have accomplished a heterogeneous Pd/C-catalyzed aqueous dehydrogenation of 1,4-cyclohexadienes and cyclohexenes to give the corresponding highly-functionalized arenes. Furthermore, various arenes could be efficiently constructed in a one-pot manner via a Diels-Alder reaction and the following dehydrogenation.

Regioselective reductive opening of substituted phthalans: synthetic applications

The reductive opening of substituted phthalans 6, 11, 12, 20, 21 and 28 with lithium and a catalytic amount of DTBB leads to the formation of corresponding functionalised organolithium intermediates 8, 15, 16, 23, 25 and 29+30 in a regioselective manner. The further reaction of these dianions with different electrophiles, mainly carbonyl compounds, gives the expected functionalised benzylic alcohols 9, 17, 18, 24, 26 and 31+32. The observed stereochemistry can be easily explained taking into account the values of the electron densities deduced by semiempirical PM3 calculations.

Regiochemistry in the reductive opening of phthalan derivatives

The lithiation of phthalan derivatives 4, 9 and 12 with an excess of lithium in the presence of a catalytic amount of 4,4′-di-tert-butylbiphenyl (DTBB) in THF at -78 °C gives dianionic intermediates 5, 10 and 13, respectively, which by reaction with different electrophiles [H2O, t-BuCHO, Me2CO, (EtO)2CO] at the same temperature, followed by hydrolysis, leads to regioselective functionalised naphthalenes 7, and biphenyls 11 and 14. The reductive opening takes place with high or total regioselectivity and can be explained considering the electron density in the dianion or in the radical anion, which are formed previous to the carbon-oxygen bond excision. The lithiation of the dihydrofurophthalan derivative 18 with the same reaction mixture but at higher temperature (0 °C) leads to intermediates 19 and 20, resulting from a single and a double reductive cleavage, respectively, which after addition of H2O and benzaldehyde as electrophiles gives a mixture of compounds 21 and 22.