3722-76-7

Upstream product

• 91319-48-1 3-(2-fluoro-5-methoxyphenyl)propanol 
• 118943-21-8 3-(4-methoxyphenoxy)-1-propanol 
• 5406-18-8 3-(p-methoxyphenyl)-1-propanol 
• 591-31-1 3-methoxy-benzaldehyde 
• 33877-04-2 ethyl (E)-3-(3-methoxyphenyl)acrylate 
• 7252-82-6 3-(3-methoxyphenyl)propan-1-ol 
• 91319-44-7 2-(2-Fluoro-5-methoxy-benzyl)-malonic acid diethyl ester 
• 91319-46-9 3-(2-fluoro-5-methoxyphenyl)propanoic acid 
• 91319-42-5 2-(bromomethyl)-1-fluoro-4-methoxybenzene 
• 17332-11-5 2-bromo-4-methoxyphenol 
• 150-76-5 4-methoxy-phenol 
• 146175-93-1 3-(2'-bromo-5'-methoxyphenyl)propanal 
• 4897-68-1 2-iodo-4-methoxybromobenzene 
• 766-85-8 3-methoxy-1-iodobenzene 

Relevant academic research and scientific papers

Nucleophilic attack of intramolecular hydroxyl groups on electron-rich aromatics using hypervalent iodine(III) oxidation

The hypervalent iodine(III) reagent, phenyliodine bis(trifluoroacetate) (PIFA)-mediated oxidative nucleophilic substitution of electron-rich aromatics involving aromatic cation radical intermediates was utilized in the direct aromatic carbon-oxygen bond f

Synthesis of Functionalized Indolines and Dihydrobenzofurans by Iron and Copper Catalyzed Aryl C-N and C-O Bond Formation

A simple and effective one-pot, two-step intramolecular aryl C-N and C-O bond forming process for the preparation of a wide range of benzo-fused heterocyclic scaffolds using iron and copper catalysis is described. Activated aryl rings were subjected to a highly regioselective, iron(III) triflimide-catalyzed iodination, followed by a copper(I)-catalyzed intramolecular N-or O-arylation step leading to indolines, dihydrobenzofurans, and six-membered analogues. The general applicability and functional group tolerance of this method were exemplified by the total synthesis of the neolignan natural product, (+)-obtusafuran. DFT calculations using Fukui functions were also performed, providing a molecular orbital rationale for the highly regioselective arene iodination process.

Synthesis of Functionalized Dihydrobenzofurans by Direct Aryl C?O Bond Formation under Mild Conditions

A method for the synthesis of dihydrobenzofurans by a direct aryl C?O bond formation is described. A mechanistic pathway for the reaction, distinct from previously described similar transformations, allows for mild reaction conditions that are expected to be compatible with functionalized substrates.

Synthesis of enantiopure (S)-7-hydroxy-3-amino-3,4-dihydro-2H-1-benzopyran en route to (+)-scyphostatin

(S)-7-Hydroxy-3-amino-3,4-dihydro-2H-1-benzopyran, a key synthetic intermediate towards the total synthesis of (+)-scyphostatin, has been prepared in >98% ee. Key synthetic steps were (i) the oxidative dearomatization of an l-tyrosine derived phenol, (ii)

Direct functionalization of arenes by primary alcohol sulfonate esters catalyzed by gold(III)

Alkylation of arenes by primary alcohol triflate or methanesulfonate esters can be efficiently catalyzed by AuCl3 with silver triflate. Copyright

Palladium-catalyzed intramolecular C-O bond formation

A number of oxygen heterocycles were synthesized using the palladium-catalyzed intramolecular etherification of aryl halides by employing di-tert-butylphosphinobiaryl ligands. The reaction proceeds under mild conditions using weak bases such as Cs2CO3 or K3PO4. A variety of functional groups are tolerated in the reaction, and enantioenriched alcohols can be coupled without erosion of optical purity. The mildness of the reaction conditions allows for the use of polyfunctionalized substrates. This method was used as the key step in the synthesis of MKC-242, an antidepressant currently in clinical trials. The synthesis of MKC-242 was achieved in 40% overall yield from commercially available sesamol and acrylonitrile.

Reactions of γ-arylalkanols via aryl radical cation and alkoxyl radical intermediates. Part 3. Reactions of 3-arylprop-1-yl hydroperoxides with iron(II) in the presence of copper(II)

A strategy for comparing the 1,5- and 1,6-cyclisation reactions of 3-phenylpropan-1-oxyl radicals is described.Iron(II)-catalysed reduction of 3-(p-methylphenyl)prop-1-yl hydroperoxide and its para-chloro and para-methoxy-substituted analogues, carried out in the presence of copper(II), has been found to give in each case the appropriate para-substituted 3-phenylpropan-1-ol, 3-phenylpropanal and a low yield of a mixture of isomeric 6- and 7-substituted chromans.The alcohols are proposed to form via reduction of either the hydroperoxide or the resulting alkoxyl radical or its cyclised intermediates, and the aldehydes as a result of rearrangement of the alkoxyl radical to an α-hydroxy alkyl radical which subsequently undergoes oxidation.The 7-substituted chromans, which arise directly from 1,6-cyclisation of the alkoxyl radical, were found to dominate the 6-substituted isomers which result from rearrangement of 1,5-cyclised intermediates.This effect is attributed to inefficient interception of the 1,5-cyclised radical intermediate which permits equilibration to the thermodynamically more stable 1,6-cyclised radical isomer to occur.The effect of pH on the reactions has been investigated and although no products typical of the intermediacy of aryl radical cations were detected (even under highly acidic conditions), the formation of such intermediates cannot be excluded.Semiempirical MO calculations have been carried out (at the PM3 level of approximation) on a series of model compounds, yielding results which have clarified our understanding of the effect of substituents on the stabilities of the various intermediates arising from the cyclisation reactions of 3-phenylpropan-1-oxyl radicals.Furthermore, these calculations have supported our assumptions regarding the probability and specificity of rearrangements of the spirodienyl intermediates.

Relevance of Conformational Constraints to the Regioselective Lithiation of Aromatic Diethers. Application to the Convenient Construction of the DEF Tricyclic Subunit of the Austalides

The lithiation of 29 and 30 is shown to occur at all three sites with a dissimilar kinetic preference.For the dihydrofuran, reaction at the proton labeled Hβ' operates predominantly; in the dihydropyran example, Hα is the favored sit

A CYCLIZATION-TRAPPING ROUTE TO CARBOCYCLIC AND HETEROCYCLIC BENZYLIC SULFONES

Acetals of 4-arylbutyraldehydes and 3-aryloxy-, 3-arylamino- and 3-arylthiopropionaldehydes react with Na-sulfinates in formic or trifluoroacetic acid to give good yields of the corresponding 4-(sulfonyl) substituted tetralins, tetrahydroquinolines, chrom