2674-44-4

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 50, p. 1259, 1985 DOI: 10.1021/jo00208a020

InChI:InChI=1/C15H12O2/c16-15-13-9-5-4-8-12(13)10-14(17-15)11-6-2-1-3-7-11/h1-9,14H,10H2

Upstream product

• 100954-88-9 (+/-)-cis-4-chloro-3-phenyl-isochroman-1-one 
• 100954-88-9 (+/?)-trans-4-chloro-3-phenylisochroman-1-one 
• 85370-71-4 N,N-diethyl-2-(2'-hydroxy-2'-phenylethyl)benzamide 
• 118-90-1 ortho-methylbenzoic acid 
• 100-52-7 benzaldehyde 
• 3469-06-5 benzocyclobutenone 
• 71885-44-4 4,5-dihydro-4,4-dimethyl-2-(2-methylphenyl)-2-oxazoline 
• 172422-08-1 α-cyanophenyl-2 phenyl-1 ethanol 
• 38453-85-9 2-[2-(hydroxymethyl)phenyl]-1-phenylethanol 
• 29539-18-2 (+/-)-3-phenylisochroman 
• 7115-91-5 2-ethoxycarbonylbenzyl bromide 
• 496-14-0 1,3-dihydroisobenzofuran 
• 100-42-5 styrene 
• 88-67-5 2-Iodobenzoic acid 

Downstream Products

• 4505-48-0 2-phenylindene 
• 85741-17-9 2-amino-3-phenyl-1,2,3,4-tetrahydroisoquinoline hydrochloride 
• 85741-19-1 [1-(4-Nitro-phenyl)-meth-(E)-ylidene]-(3-phenyl-3,4-dihydro-1H-isoquinolin-2-yl)-amine 
• 85741-16-8 2-Nitroso-3-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 55150-54-4 1-chloro-3-phenylisoquinoline 
• 7115-13-1 3-phenyl-2H-isoquinolin-1-one 
• 78318-00-0 3-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 4809-08-9 3-phenyl-isocoumarin 
• 38453-85-9 2-[2-(hydroxymethyl)phenyl]-1-phenylethanol 
• 60901-21-5 o-styrylbenzoic acid 
• 4890-85-1 o-phenethylbenzoic acid 

Relevant academic research and scientific papers

Visible Light-Promoted Magnesium, Iron, and Nickel Catalysis Enabling C(sp3)-H Lactonization of 2-Alkylbenzoic Acids

A mild and practical C(sp3)-H lactonization protocol has been achieved by merging photocatalysis and magnesium (iron, nickel) catalysis. A diverse range of 2-alkylbenzoic acids with a variety of substitution patterns could be transformed into the corresponding phthalide products. Based on the mechanistic experimentation and reported prior studies, a possible mechanism for the benzylic oxidative lactonization reaction was proposed with the hypothetic photoactive ternary complex formed between the 2-alkylbenzoic acid substrate, magnesium ion, and bromate anion.

Metal-Free Addition of Benzyl Halides to Aldehydes Using Super Electron Donors: Access to 3,4-Dihydroisocoumarins and 1,2-Diarylethanols

We report here the intermolecular metal-free addition reaction of functionalized benzyl halides to aldehydes using a super electron donor (SED). The metal-free and mild conditions allowed the formation of 3,4-dihydroisocoumarins and 1,2-diarylethanols with unprecedented functional group tolerance.

Calcium(II)- And Triflimide-Catalyzed Intramolecular Hydroacyloxylation of Unactivated Alkenes in Hexafluoroisopropanol

We report an efficient intramolecular hydroacyloxylation of unactivated alkenes, offering a streamlined access to relevant γ-lactones, which features the utilization of either a calcium(II) salt or triflimide as a catalyst in hexafluoroisopropanol. This method could be applied to the synthesis of natural products and the late-stage functionalization of natural and bioactive molecules. Additionally, DFT computations were used to elucidate the twist of reactivity observed between the hydroamidation and hydroacyloxylation of unactivated alkenes regarding the formation of 5- and 6-membered rings.

Cooperative iodine and photoredox catalysis for direct oxidative lactonization of carboxylic acids

A new method for the formation of γ- and δ-lactones from carboxylic acids through direct conversion of benzylic C-H to C-O bonds is described. The reaction is conveniently induced by visible light and relies on a mild cooperative catalysis by the combination of molecular iodine and an organic dye.

Palladium/Acid Relay Catalyzed Tandem Heck Coupling/6-Endo Cyclization between ortho-Halogenated Benzoates and Unactivated Terminal Alkenes for the Synthesis of 1-Isochromanones

We report a unique and expeditious route to synthesize 1-isochromanone derivatives through palladium catalyzed tandem Heck coupling/6-endo hydroacyloxylation cyclization between readily available ortho-halogenated benzoates and unactivated alkenes. Various 2-bromo or 2-iodo benzoates can be coupled efficiently with a broad range of alkenes to afford functionalized 1-isochromanones in high yields. Significantly, this cost-efficient and easy-to-handle synthetic methodology will have great prospect application in the synthetic and medicinal chemistry. (Figure presented.).

First TDAE Reactivity Using Benzonitrile Derivatives as Substrates and Its Application to the Synthesis of 3-Substituted Isochroman-1-ones

The first TDAE-initiated reaction between benzonitrile derivatives as substrates and substituted benzaldehydes to form substituted hydroxyethylbenzonitrile derivatives is reported. The 2-hydroxyethyl benzonitrile derivatives thus formed were good candidat

Photoinduced Regioselective Lactonization of ortho-Iodobenzoic Acids with Alkenes: Synthesis of 3,4-Dihydroisocoumarin Derivatives

A photoinduced strategy for the synthesis of a variety of 3,4-dihydroisocoumarins has been realized. The reactions proceeded from ortho -iodobenzoic acids and alkenes through a photodehalogenative lactonization with NaHCO 3 as the only additive in dimethyl sulfoxide (DMSO) to provide the desired products in moderate to good yields. This method offers a simple, mild, and environmentally friendly route to 3,4-dihydroisocoumarin derivatives.

Visible-Light-Induced C-O Bond Formation for the Construction of Five- and Six-Membered Cyclic Ethers and Lactones

Visible-light-induced intramolecular C-O bond formation was developed using 2,4,6-triphenylpyrylium tetrafluoroborate (TPT), which allows the regiocontrolled construction of cyclic ethers and lactones. The reaction is likely to proceed through the single-electron oxidation of the phenyl group, followed by the formation of a benzylic radical, thus preventing a competing 1,5-hydrogen abstraction pathway. Detailed mechanistic studies suggest that molecular oxygen is used to trap the radical intermediate to form benzyl alcohol, which undergoes cyclization. This new approach serves as a powerful platform by providing efficient access to valuable five- and six-membered cyclic ethers and lactones with a unified protocol.

Scalable Electrochemical Dehydrogenative Lactonization of C(sp2/sp3)-H Bonds

A practical, electrochemical method is developed for the direct dehydrogenative lactonization of C(sp2/sp3)-H bonds under external oxidant- and metal-free conditions, delivering diverse lactones, including coumarin derivatives with excellent regioselectivity. The scalable nature of this newly developed electrochemical process was demonstrated on a 40 g scale following an operationally simple protocol. The remote lactonization of C(sp3)-H bonds would constitute an important synthetic advance toward electrochemical C-O bond formation.

Cobalt-Catalyzed Coupling of Benzoic Acid C?H Bonds with Alkynes, Styrenes, and 1,3-Dienes

A method for cobalt-catalyzed, carboxylate-directed functionalization of arene C?H bonds is reported. Alkynes, styrenes, and 1,3-dienes can be coupled with benzoic acids to provide cyclic products in good yields. The reactions proceed in the presence of a