23020-47-5

Upstream product

• 14305-29-4 3-hydroxy-1-(4-methoxyphenyl)-3-methylbutane 
• 100-66-3 methoxybenzene 
• 78-79-5 isoprene 
• 824-94-2 p-methoxybenzyl chloride 
• 115-11-7 isobutene 
• 104-20-1 4-(4-methoxyphenyl)-2-butanone 

Downstream Products

• 3123-97-5 dihydro-5,5-dimethyl-2(3H)-furanone 
• 4957-18-0 1-methoxy-4-(3-methyl-but-2-enyl)benzene 
• 14305-29-4 3-hydroxy-1-(4-methoxyphenyl)-3-methylbutane 
• 18491-21-9 1-methoxy-4-(3-methylbut-3-en-1-yl)benzene 
• 184779-69-9 1-Methoxy-4-[3-methyl-3-(2,2,2-trifluoro-ethoxy)-butyl]-benzene 
• 1615227-20-7 2-(4-(4-methoxyphenyl)-2-methylbutan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Relevant academic research and scientific papers

Ti-Catalyzed Radical Alkylation of Secondary and Tertiary Alkyl Chlorides Using Michael Acceptors

Alkyl chlorides are common functional groups in synthetic organic chemistry. However, the engagement of unactivated alkyl chlorides, especially tertiary alkyl chlorides, in transition-metal-catalyzed C-C bond formation remains challenging. Herein, we describe the development of a TiIII-catalyzed radical addition of 2° and 3° alkyl chlorides to electron-deficient alkenes. Mechanistic data are consistent with inner-sphere activation of the C-Cl bond featuring TiIII-mediated Cl atom abstraction. Evidence suggests that the active TiIII catalyst is generated from the TiIV precursor in a Lewis-acid-assisted electron transfer process.

Manganese-Catalyzed Borylation of Unactivated Alkyl Chlorides

The use of low-cost manganese(II) bromide (MnBr2) and tetramethylethylenediamine (TMEDA) catalyzes the cross coupling of (bis)pinacolatodiboron with a wide range of alkyl halides, demonstrating the first manganese-catalyzed coupling with alkyl electrophiles. This method allows access to primary, secondary, and tertiary boronic esters from the parent chlorides, which were previously inaccessible as coupling partners. The reaction proceeds in high yield with as little as 1000 ppm catalyst loading, while 5 mol % can provide high yields in as little as 30 min. Finally, radical-clock experiments revealed that at 0 °C direct borylation outcompetes alternative radical processes, thereby providing synthetically useful, temperature-controlled reaction outcomes.

Iron-catalyzed borylation of alkyl electrophiles

The use of low-cost iron(III) acetoacetate (Fe(acac)3) and tetramethylethylenediamine (TMEDA) enables the direct cross-coupling of alkyl halides with bis(pinacolato)diboron. This approach allows for the borylation of activated or unactivated primary, secondary, and tertiary bromides. Moreover, even the borylation of benzylic or allylic chlorides, tosylates, and mesylates are possible. The reactions proceed under mild conditions at room temperature and show broad functional-group compatibility and "robustness" as measured by a modified Glorius robustness screen.

Mechanism for nucleophilic substitution and elimination reactions at tertiary carbon in largely aqueous solutions: Lifetime of a simple tertiary carbocation

The rate constants and the yields of the products of the nucleophilic substitution and elimination reactions of 1-(4-methoxyphenyl)-3-methyl-3-butyl derivatives (1-X) have been determined in mostly aqueous solvents, and the absolute rate constant for reac

SYNTHESIS OF γ-LACTONES FROM ALKENES EMPLOYING p-METHOXYBENZYL CHLORIDE AS (1+)CH2-CO2(1-) EQUIVALENT

The ZnCl2 catalyzed reaction of p-methoxybenzyl chloride with alkenes yields the 1:1 addition products 3, which are converted into the γ-lactones 4 via Ru(VIII) catalyzed oxidative degradation of the aromatic ring.