1287655-99-5

Upstream product

• 70-55-3 toluene-4-sulfonamide 
• 70396-10-0 (Z)-3-iodo-2-phenyl-prop-2-en-1-ol 
• 100-58-3 phenylmagnesium bromide 

Downstream Products

• 1287656-32-9 C₂₀H₂₂INO₂S 
• 1287656-34-1 C₂₃H₂₈INO₂S 
• 1287656-39-6 C₂₃H₂₈INO₂S 
• 1287656-42-1 C₂₈H₂₈INO₄S 
• 1287656-44-3 C₂₈H₃₀INO₃S 
• 1287656-49-8 C₂₀H₂₃NO₂S 
• 1287656-53-4 C₂₀H₂₃NO₃S 
• 1287656-56-7 C₂₀H₂₂N₄O₂S 
• 1287656-58-9 C₂₁H₂₃NO₃S 
• 1287656-24-9 C₂₈H₂₈INO₄S 
• 1287656-52-3 C₂₃H₂₇⁽²⁾HINO₂S 
• 1287656-16-9 C₂₃H₂₈INO₂S 
• 1287656-18-1 C₂₃H₂₈INO₂S 
• 1287656-25-0 C₂₈H₃₀INO₃S 

Relevant academic research and scientific papers

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 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 cycloisomerizations of (Z)-1-iodo-1,6-dienes: Iodine atom transfer and mechanistic insight to alkyl iodide reductive elimination

A palladium-catalyzed iodine atom transfer cycloisomerization of (Z)-1-iodo-1,6-diene has been developed, which provides a facile method to construct six-memebered heterocycles bearing an alkyl iodide group. The ligand screening shows that both the type and the quantity of ligand impose significant influences on this transformation, and the combination of 30 mol % 1,1′-bis(diphenylphosphino)ferrocene (DPPF) and 10 mol % Pd(OAc) 2 is the optimal choice. The catalytic cycle, consisting of oxidative addition of Pd(0) to vinyl iodide, intramolecular alkene insertion, and alkyl iodide reductive elimination, has been proposed and eventually supported by convincing evidence from a series of control experiments. More importantly, these control experiments disclose some features of the event of alkyl iodide reductive elimination: (1) this reductive elimination is proved to be a stereospecific process; and (2) both alkyl iodide oxidative addition and reductive elimination are not effected by a TEMPO additive. Besides its ability to undergo oxidative addition, the catalyst (palladium + DPPF) could also promote a radical transfer process. The findings described in this paper will be helpful for further development of the metal-catalyzed formation of a carbon-halide bond.

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.