40904-92-5

Upstream product

• 578-57-4 2-bromoanisole 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 767-91-9 1-ethynyl-2-methoxybenzene 
• 67-64-1 acetone 
• 529-28-2 4-iodoanisol 
• 100-66-3 methoxybenzene 
• 29552-15-6 4-chloro-2-methylbut-3-yn-2-ol 
• 40888-07-1 1-[3-(1-Ethoxy-ethoxy)-3-methyl-but-1-ynyl]-2-methoxy-benzene 

Downstream Products

• 1117722-82-3 C₁₆H₁₄O₂ 
• 1611477-64-5 3-(2-methoxyphenyl)-5,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-oxaborol-2(5H)-ol 
• 136612-77-6 (E)-2,2'-(but-1-en-3-yne-1,4-diyl)bis(methoxybenzene) 
• 33560-74-6 1,4-bis(2-methoxyphenyl)-1,3-butadiyne 
• 1448422-11-4 1-(2-methoxyphenyl)-1,3-octadiyne 
• 1231218-93-1 2-[(2-methoxyphenyl)buta-1,3-diyn-1-yl]naphthalene 

Relevant academic research and scientific papers

Synthesis of 3-selanylbenzo[: B] furans promoted by SelectFluor

A simple and practical protocol for the synthesis of 3-selanyl-benzo[b]furans mediated by the SelectFluor reagent was developed. This novel methodology provided a greener alternative to generate 3-substituted-benzo[b]furans via a metal-free procedure unde

Palladium(II)/Lewis acid cocatalyzed oxidative annulation of 2-alkenylanilines and propargylic esters: An access to benzo[ b]azepines

An attractive approach to valuable yet synthetically challenging benzo[b]azepines was established via palladium(II)/Lewis acid cocatalyzed oxidative [5 + 2] annulation of readily available 2-alkenylanilines and propargylic esters. The protocol features mild reaction conditions and good functional group tolerance, constituting an array of benzo[b]azepines in yields of 30-75%.

Asymmetric Intermolecular Heck Reaction of Propargylic Acetates and Cycloalkenes to Access Fused Cyclobutenes

An asymmetric Heck annulation of propargylic acetates with several types of cyclic olefins affords highly strained cyclobutenes in high enantioselectivity.

Iron-Promoted Tandem Cyclization of 1,3-Diynyl Chalcogen Derivatives with Diorganyl Dichalcogenides for the Synthesis of Benzo[b]furan-Fused Selenophenes

A double intramolecular 5-endo-dig cyclization of butyl[2-(phenylbuta-1,3-diynyl)phenyl]chalcogens has been employed in a selective preparation of benzo[b]chalcogenopheno[2,3-d]furans. Several reaction parameters were studied to determine the best reaction conditions and we observed that the reaction of butyl[2-(phenylbuta-1,3-diynyl)phenyl]chalcogens (0.25 mmol) with iron(III) chloride hexahydrate (2.0 equiv.) and diorganyl diselenides (1.75 equiv.) at reflux of dichloromethane was the most appropriate to give the products in 35–89% yields. These standard reaction conditions were compatible with many functional groups in the substrates, such as methyl, chlorine, fluorine, methoxy and heteroaryl. This protocol was also efficient for diorganyl diselenides but it was ineffective with diorganyl disulfides and ditellurides. In a competition among selenium, sulfur and oxygen nucleophiles we observed that the nucleophilicity and steric effects of the competing functional groups were determinant factors for the selectivity of the cyclization. The benzo[b]chalcogenopheno[2,3-d]furans had absorptions in the UV region (300–350 nm range) with molar absorptivity coefficient values ascribed to spin and symmetry allowed π–π* electronic transitions. An emission located in the purple region (380–440 nm range), with a Stokes shift of between 65–100 nm, is probably associated to the charge transfer character of the excited state. (Figure presented.).

Regio- and stereoselective dimerization of arylacetylenes and optical and electrochemical studies of (E)-1,3-enynes

The N-heterocyclic carbene palladium complex (SIPr)Pd(cinnamyl)Cl [SIPr=N,N'-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene) promotes regio- and stereospecific dimerization of a variety of arylalkynes to give (E)-1,3-enynes in good to excellent yields. An efficient and practical procedure for their synthesis was developed using a biphasic aqueous alkali/heptane system. Optical and electronic properties of (E)-1,3-enynes are highly tunable. Depending on the nature of the substituents, HOMO energies vary in the range 5.3-6.0eV. (E)-1,3-Enynes can exhibit intense photoluminescence in the spectral region 350-500nm.

An approach to the selenobromination of aryl(thienyl)alkynes: Access to 3-bromobenzo[b]selenophenes and selenophenothiophenes

A novel approach for the cyclization of arylalkynes with selenium(IV) bromide prepared in situ has been elaborated. The use of an alkene additive as a bromine scavenger provides a convenient synthetic pathway for the synthesis of a wide variety of 3-bromobenzo[b]selenophenes. Reactions can be performed open to air without the use of moisture-sensitive reagents, anhydrous solvents, or an inert atmosphere. Selenobromination of ethynylthiophenes has been applied for the preparation of selenopheno[3,2-b]- and selenopheno[2,3-b]thiophenes. The molecular structures of representative derivatives have been confirmed by X-ray crystallographic analysis. The use of an alkene additive as a bromine scavenger under selenobromination conditions provides a convenient synthetic pathway for the synthesis of a wide variety of 3-bromobenzo[b]selenophenes in moderate to high yields. The reactions are not moisture-sensitive and do not require an inert atmosphere. Selenobromination of ethynylthiophenes enables the preparation of selenopheno[b]thiophenes. Copyright

Simple and practical one-step synthesis of new 1,3-dienic δ-sultones from terminal alkynes and some synthetic applications of these compounds

1,3-Dienic δ-sultones 4,6-diaryl-[1,2]oxathiine 2,2-dioxides were synthesized via a one-step reaction of arylalkynes with dioxane sulfotrioxide. The reactivity of various alkynes in this reaction was investigated. The resulting sultones were brominated with Br2 or N-bromosuccinimide regioselectively to sulfur and subsequently coupled with phenylacetylene using Sonogashira conditions.

Three types of products by carbon nucleophiles toward methoxyphenylacetylenic sulfones

Methoxy-arylacetylenic sulfones were examined to react with various carbanion nucleophiles to result in the three types of products; thus, (i) nucleophiles (MeLi·LiBr, Vinyl MgBr, LiCH2CN) showed the α-addition, however, (ii) Li-CC-TMS afforded β-addition (conjugate addition) products. The (iii) displacement reaction through α-addition/ isomerization/trans-elimination was enhanced by the presence of ortho-methoxy group at high temperature. The heteroatom nucleophiles (nitrogen, oxygen or sulfur atom) in a protic solvent provided only conjugate addition products as reported.

Simple, convenient, and efficient synthesis of 2-aryl-substituted benzo[b]furans

A simple, convenient, and efficient one-pot method for the preparation of benzofuran is reported. Sonogashira coupling reaction of aryl iodides with 2-methyl-3-butyn-2-ol was used as an acetylene source in the presence of Pd(PPh3)2Cl2 and CuI. Deprotection of the acetylene moiety in the same pot using a strong base and the second Sonogashira coupling/cyclization of and substituted o-iodophenols led to the formation of the appropriate benzo[b]furans. These protocols also can be used in the synthesis of natural products and indoles. Copyright Taylor & Francis Group, LLC.

Electrophilic cyclization of 2-chalcogenealkynylanisoles: Versatile access to 2-chalcogen-benzo[b]furans

An efficient synthesis of 2-ehalcogen-3-substituted-benzo[b]furan compounds has been accomplished via electrophilic cyclization reaction of 2-chalcogenealkynyl anisoles using I2, ICl, Br2, and PhSeBr as electrophile sources. The product distributions were strongly dependent on the nature of substituents in the aromatic ring of anisole and on the chalcogen atom directly bonded to the triple bond. The 2-chalcogen-3-iodo- benzo[b]furans obtained smoothly underwent conversion to more complex structures of benzo-[b]furan derivatives via palladium- or copper-catalyzed cross-coupling reaction with thiols, diphenyl diselenides, and zincates.