5073-13-2

Upstream product

• 4437-24-5 1-phenyl-3-(2-furyl)prop-1-yne 
• 2207-63-8 3-(2-furyl)-1-phenyl-1-propanone 
• 502-22-7 benzyl(2-furyl)acetylene 
• 110-00-9 furan 
• 637-59-2 1-Bromo-3-phenylpropane 
• 623-30-3 3-furan-2-yl-propenal 
• 108-86-1 bromobenzene 
• 39763-89-8 2-(2-phenyl-cyclopropyl)-furan 
• 617-88-9 2-Chloromethylfuran 
• 39511-12-1 (E)-3-(furan-2-yl)-1-phenyl-2-propen-1-one 
• 18649-64-4 2-ethynylfuran 
• 1217485-28-3 7-phenyl-3-heptyne-1,5-diol 
• 1323325-30-9 1-phenyl-7-(tetrahydro-2H-pyran-2-yloxy)hept-4-yn-3-ol 
• 1338347-55-9 C₂₅H₃₀O₅S 

Downstream Products

• 5120-10-5 (+/-)(1Ξ,2Ξ)-1-(3-phenyl-propyl)-7-oxa-norborn-5-ene-2r,3c-dicarboxylic acid-anhydride 
• 128912-44-7 2,5-Bis-(3-phenyl-propyl)-furan 
• 179618-54-3 (2E)-7-phenyl-4-oxo-2-heptenal 
• 1821-12-1 4-Phenylbutyric acid 

Relevant academic research and scientific papers

From Dimethylamine to Pyrrolidine: The Development of an Improved Nickel Pincer Complex for Cross-Coupling of Nonactivated Secondary Alkyl Halides

Replacement of a dimethyl amino group of the amidobis(amine) nickel(II) pincer complex (1), [(MeN2N)Ni-Cl], by a pyrrolidino group resulted in a new nickel(II) pincer complex (2), [(PyrNMeNN)Ni-Cl]. Complex 2 is an efficient catalyst for Kumada and Suzuki-Miyaura cross-coupling of nonactivated secondary alkyl halides, while complex 1 is largely inactive. The significant activity difference is tentatively attributed to a minimal structural difference, which leads to a more hemilabile ligand.

Suzuki-miyaura cross-coupling reactions of unactivated alkyl halides catalyzed by a nickel pincer complex

A nickel(II) pincer complex, [(MeN2N)Ni-Cl], was used to catalyze alkyl-alkyl and alkyl-aryl Suzuki-Miyaura coupling reactions of unactivated alkyl halides. The coupling of 9-alkyl-9-borabicyclo[3.3.1]nonane and 9-phenyl-9-borabicyclo[3.3.1]nonane reagents with alkyl halides was achieved in modest to good yields. The reactions tolerated a variety of useful functional groups including ester, ether, furan, thioether, acetal, and Boc groups. Georg Thieme Verlag Stuttgart, New York.

Generation of α,β-unsaturated platinum carbenes from homopropargylic alcohols: Rearrangements to polysubstituted furans

A number of diversely substituted furans are synthesized via a cycloisomerization process that goes through a unique metal carbene species. Both ligand structure and the nature of the leaving group are evaluated. The characteristics of the carbene intermediate can be modulated, resulting in highly selective hydrogen or silicon group migrations.

Efficient conditions for conversion of 2-substituted furans into 4-oxygenated 2-enoic acids and its application to synthesis of (+)-aspicilin, (+)-patulolide a, and (-)-pyrenophorin

2-Substituted furans 1a,b,c were found to be conveniently transformed into trans 4-oxo-2-enals 2a,b,c in 62-87% yields by using NBS/pyridine in THF-acetone-H2O (3 in acetone-H2O (2 led to the trans 4-oxo-2-enoic acids 3a-c in good yields. With this transformation in mind, we designed syntheses of (+)-aspicilin, (+)-patulolide, and (-)-pyrenophorin. In the synthesis of (+)-aspicilin as shown in Schemes 1 and 2, the pivotal intermediate 6 was prepared from olefin 7 in which 2-furyl group is attached. The AD reaction of 7 secured the C(5) and C(6) stereochemistry of aspicilin, and the subsequent transformation using the protocol described above afforded the ester 6. Stereocontrolled reduction of 6 followed by deprotection and the Yamaguchi macrocyclization furnished (+)-aspicilin. For the synthesis of (+)-patulolide (Scheme 3) and (-)-pyrenophorin (Scheme 4), the intermediates are the furans 38 and 44, which were prepared easily by the classical methods using furyllithium 33. The furan ring oxidations proceeded as well, furnishing acids 40 and 46 in good yields, acetalization of which afforded the known intermediates 41 and 47, respectively.

Synthesis and Characterisation of some 1,4,8,11,15,18,22,25-Octa-alkyl- and 1,4,8,11,15,18-Hexa-alkyl-22,25-bis(carboxypropyl)phthalocyanines

A series of 3,6-dialkylphthalonitriles and 3,6-bis(4,4,4-trimethoxybutyl)phthalonitrile have been prepared via Diels-Alder reactions of 2,5-disubstituted furans or thiophene 1,1-dioxides with fumaronitrile.The phthalonitriles were converted into the title phthalocyanines as metal-free and copper(II) derivatives.The macrocycles were characterised using 1H NMR and optical spectroscopy, and fastatom bombardment spectrometry.Certain examples exhibit discotic liquid crystal behaviour.