70396-10-0

Upstream product

• 107-19-7 propargyl alcohol 
• 87295-65-6 C₉H₈MgO 
• 100-58-3 phenylmagnesium bromide 
• 108-86-1 bromobenzene 

Downstream Products

• 2699-89-0 (Z)-2,3-diphenylprop-2-en-1-ol 
• 102934-78-1 (Z)-1-iodo-2-phenyl-3-chloro-1-propene 
• 250358-91-9 (Z)-2-phenyl-5-trimethylsilanylpent-2-en-4-yn-1-ol 
• 102934-82-7 1-phenyl-2-(trimethylsilyl)cyclopropene 
• 1447908-93-1 (2R,3R,4R)-1,3,4-trimethoxy-5-(4-phenyl-2-furyl)-2-pentanol 
• 1447908-68-0 3-(4-phenyl-2-furyl)-1-propanol 
• 1447908-79-3 (Z)-3-iodo-1,2-diphenyl-2-propen-1-ol 
• 1447908-85-1 4-(4,5-diphenyl-2-furyl)-1-butanol 
• 1447908-69-1 4-(4-phenyl-2-furyl)-1-butanol 
• 1287655-99-5 C₁₆H₁₆INO₂S 
• 1585185-79-0 C₁₉H₁₈INO₂S 
• 1585185-86-9 C₁₉H₁₈INO₂S 
• 1350810-32-0 C₁₁H₁₁IO₂ 

Relevant academic research and scientific papers

Efficient Synthesis of Polysubstituted Furans through a Base-Promoted Oxacyclization of (Z)-2-En-4-yn-1-ols

An efficient base catalyzed oxacyclization of Z-enynols has been developed under transition metal-free reaction conditions, thus resulting in a variety of new di-, tri-, and tetra-substituted furans. This approach allowed us to obtain 32 new compounds. Furthermore, DFT calculations were realized to depict a relationship between the natural population analysis and experimental results with alkyl or aryl groups for the synthesis of 2-benzylfuran. A one-pot Sonogashira/oxacyclization approach offers a flexible, robust and efficient alternative to base catalyzed cyclization is also carried out.

Unified Approach to Furan Natural Products via Phosphine-Palladium Catalysis

Polyalkyl furans are widespread in nature, often performing important biological roles. Despite a plethora of methods for the synthesis of tetrasubstituted furans, the construction of tetraalkyl furans remains non-trivial. The prevalence of alkyl groups in bioactive furan natural products, combined with the desirable bioactivities of tetraalkyl furans, calls for a general synthetic protocol for polyalkyl furans. This paper describes a Michael–Heck approach, using sequential phosphine-palladium catalysis, for the preparation of various polyalkyl furans from readily available precursors. The versatility of this method is illustrated by the total syntheses of nine distinct polyalkylated furan natural products belonging to different classes, namely the furanoterpenes rosefuran, sesquirosefuran, and mikanifuran; the marine natural products plakorsins A, B, and D and plakorsin D methyl ester; and the furan fatty acids 3D5 and hydromumiamicin.

An organocatalytic method for constructing pyrroles: Via the cycloisomerisation of Z -1-iodo-4- N -methylbenzenesulfonyl-1,6-enynes

A new cycloisomerisation of Z-1-iodo-4-N-methylbenzenesulfonyl-1,6-enynes to functionalized pyrroles was realized in the presence of an organomolecule (4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine) and KOtBu. The transformations were performed efficiently to produce different kinds of functionalized pyrroles within 10 min. This is the first example of an organomolecule promoted methodology with vinyl iodides from a non-aromatic system to an aromatic system, which offers an excellent option toward establishing a new horizon for cross-coupling reactions of vinyl halides. Preliminary mechanistic studies were performed and a crude radical pathway was proposed.

Palladium-catalyzed intermolecular [4 + 2] formal cycloaddition with (Z)-3-iodo allylic nucleophiles and allenamides

A highly chemo- and regioselective [4 + 2] formal cycloaddition of (Z)-3-iodo allylic nucleophiles and allenamides catalyzed by palladium is reported. The methodology proceeds under mild reaction conditions and is tolerant of alkyl and aryl functional groups. The SN2′ substitution at the proximal C═C bond performed against the Heck or SN2 pathway delivered a variety of 2-amino-dihydropyrans and 2-amino-tetrahydropiperidines in moderate to satisfactory yields. The [4 + 2] formal cycloaddition derivatives are convertible to interesting scaffolds 2,6,7,7a-tetrahydropyrano[2,3-b]pyrrole and 2,6,7,7a-tetrahydro-1H-pyrrolo[2,3-b]pyridine derivatives via ring-closing metathesis (RCM) with Grubbs catalyst II.

Palladium-catalyzed heck-type cascade cyclization of (Z)-1-iodo-1,6-dienes with N-tosyl hydrazones

A palladium-catalyzed heck-type cascade cyclization of (Z)-1-iodo-1,6-dienes with N-tosyl hydrazones is reported. The alkylpalladium intermediate coupled with the diazo compound, generating the second alkylpalladium species bearing two β-H, which generate

Intramolecular cascade rearrangements of enynamine derived ketenimines: Access to acyclic and cyclic amidines

Copper-catalyzed reaction of enynamines with sulfonylazides provides acyclic and cyclic amidines. Nucleophilic addition of the tethered amino group on the in situ generated ketenimine forms a six-membered cyclic zwitterionic intermediate which facilitates

Palladium-catalyzed cyclization of vinyl iodide-tethered allensulfonamide

This Letter describes a palladium-catalyzed cyclization of vinyl iodide-tethered allensulfonamide in the presence of alkylol, which provides a facile access to 2-alkoxy-3-methylene-tetrahydropyridine. The asymmetric version of this reaction has also been preliminarily realized with up to 81% enantioselectivity when chiral bisphosphine ligands were used.

Synthesis of 3-pyrroline via domino Heck-aza-Michael reaction

This Letter describes the Pd(0)-catalyzed domino Heck-aza-Michael reaction between (Z)-N-(3-iodoallyl)-tosylamide and acrylic ester. The reaction provides a facile access to an important class of substituted 3-pyrroline.

Palladium-catalyzed Heck-type reaction of oxime ether bearing a pendant vinyl iodide moiety

A Pd(0)-catalyzed intramolecular Heck-type reaction of oxime ether has been developed, providing convenient access to heterocyclic oximes. The Royal Society of Chemistry 2011.

Synthesis of isocoumarins and α-pyrones via palladium-catalyzed annulation of internal alkynes

A number of 3,4-disubstituted isocoumarins and polysubstituted α- pyrones have been prepared in good yields by treating halogen- or triflate- containing aromatic and α,β-unsaturated esters, respectively, with internal alkynes in the presence of a palladiu