20871-31-2

Upstream product

• 136918-14-4 phthalimide 
• 770-09-2 benzyltrimethylsilane 
• 108-88-3 toluene 
• 13005-36-2 potassium phenylacetate 
• 100-39-0 benzyl bromide 
• 1589-82-8 phenylmagnesium bromide 

Downstream Products

• 104563-06-6 3-Benzyl-3-(4-hydroxy-phenyl)-2,3-dihydro-isoindol-1-one 
• 39142-91-1 3-benzyl-2,3-dihydro-1H-isoindolin-1-one 
• 40523-32-8 3-(phenylmethylene)isoindol-1-one 
• 764669-06-9 (R)-3-benzylisoindolin-1-one 
• 33608-93-4 (E)-2,3-dihydro-3-phenylmethylene-1H-isoindol-1-one 

Relevant academic research and scientific papers

Erratum: Continuous-Flow Photochemical Transformations of 1,4-Naphthoquinones and Phthalimides in a Concentrating Solar Trough Reactor (Aust. J. Chem. (2020) 73(12):1149-1157)

The authors wish to advise of errors in the above paper. In Table 3, footnote C should read 'Crude product contains 4-methylanisole or p-tolyl acetate.' In the left column of text on the same page as Table 3, the second last sentence should read 'When the para-substituted arylacetates 9b and 9c were employed, 4-methylanisole and p-tolyl acetate were detected by 1H NMR analysis of the crude reaction mixtures but no attempts were made to isolate these simple decarboxylation products.'

Enantioselective Hydrophosphonylation of in Situ Generated N-Acyl Ketimines Catalyzed by BINOL-Derived Phosphoric Acid

An efficient route to pharmacologically interesting isoindolinone-based α-amino phosphonates is described via asymmetric hydrophosphonylation of in situ generated ketimines catalyzed by BINOL-derived phosphoric acid. The reaction proceeds smoothly at ambient temperature affording a variety of α-amino phosphonates with a quaternary stereogenic center embedded in isoindolinone motif in high yields with excellent enantiomeric ratios (up to 98.5:1.5 er). Several interesting transformations of the products into valuable synthetic intermediates are also depicted.

Photodecarboxylative benzylations of phthalimide in pH 7 buffer: A simple access to 3-arylmethyleneisoindolin-1-ones

Photoadditions of phenylacetates to phthalimide in pH 7 buffer solution give the corresponding benzylated-hydroxyphthalimidines in moderate to high yields of up to 94%. In a micro-structured reactor, higher conversions and purities are achieved. With branched phenylacetates, photoaddition affords diastereoisomeric mixtures with low to moderate de values. Subsequent acid-catalyzed dehydration furnishes the corresponding 3- arylmethyleneisoindolin-1-ones in good to excellent yields and with high E-selectivities. Irradiation of the parent 3-phenylmethyleneisoindolin-1-one under oxidative conditions only leads to cis/trans-isomerization.

A Practical Two-Step Synthesis of 3-Alkyl-2,3-dihydro-1H-isoindolin-1-ones

A flexible approach to 3-alkyl-2,3-dihydro-1H-isoindolin-1-ones via the reductive-alkylation procedure is described. Present method is versatile in scope, allowing the easy introduction of various C-3 carbon-substituents by Grignard addition to phthalimid

SET photochemistry of phthalimide anion and its reactivity with hydrogen donors

The investigation of the photochemistry of phthalimide anion has uncovered its exceptional reactivity with hydrogen donors such as alcohols, toluene, ethers and amines. Photoreactions can be conducted to high conversions and photoadducts are formed in high yield and with predictable regioselectivity. Exploratory studies have revealed that SET from the excited phthalimide anion to phthalimide is a thermodinamically favourable step that produces the electrophilic phthalimidyl radical and is the key step of the process.

Photochemical Reaction of Phthalimides and Dicyanophthalimides with Benzylic Donors

Irradiation of phthalimides in the presence of benzylic donors PhCRHX (R = H, Ph, X = H, SiMe3, CHPh2, proceeds via electron transfer and radical cation cleavage, resulting in benzylation at the carboximide moiety to yield 3-benzyl-3-hydroxyisoindol-3-ones.With 4,5-dicyanophthalimides substitution of benzyl for a cyano group is a competitive, and in some cases predominating, pathway.A rationalization is proposed on the basis of the in cage vs out of cage radical cation cleavage.In the first mechanism, the radical anion of the dicyanophthalimide, where spin and charge are differently located, probably assists the radical cation fragmentation.