874895-87-1

Upstream product

• 1155621-24-1 C₁₄H₂₁NO₂ 
• 826-55-1 2-methyl-2-phenylpropionic acid 
• 36293-05-7 2-methyl-2-phenylpropanoyl chloride 
• 124-68-5 2-Amino-2-methyl-1-propanol 

Downstream Products

• 1039038-37-3 2-(2-(2-iodophenyl)propan-2-yl)-4,4-dimethyl-4,5-dihydrooxazole 

Relevant academic research and scientific papers

Aryl-oxazoline chelates of first-row transition metals: Structures of {Κ-C,N-(o-C6H4)CMe2(COCH 2CMe2N)}FeCl(py) and [(Κ-C,N-(o-C6H 4)CMe2(COCH2CMe2N)}Cr(μ-Cl)] 2

Aryl-oxazoline synthons have been explored for the preparation of strong-field first-row transition metal chelate species. With 4,4-dimethyl-2-phenyloxazoline (HPhOx), no CH bond activations afforded complexation, and aside from Zn(Κ-C,N-4,4-Me2-2-(o-C 6H4)oxazoline)2 (Zn(PhOx)2), aryl-coupling reactions were noted with 4,4-dimethyl-2-(2-lithiophenyl)oxazoline (LiPhOx) and MX2; [Κ-N,N-{4,4-Me2-(2-o-C 6H4)-2-oxazoline}2]CoCl2 (1-Co) was structurally characterized. Metalations with 4,4-dimethyl-2-benzyloxazoline (PhCH2Ox) were prone to deprotonation, as exemplified by (Me 2N)3Ti(η-N-(4,4-dimethyl-(2-CHPh)oxazoline)) (2) and bis-N,N′-(4,4-dimethyl-(2-pyridylmethylyl)oxazoline)Fe (3). Oxidative addition of 4,4-dimethyl-2-(2-bromophenylpropan-2-yl)oxazoline (BrPhCMe 2Ox) to Ni(COD)2 provided [{Κ-C,N-(o-C 6H4)CMe2(COCH2CMe 2N)}Ni]2(μ-Br)2 (42). With 4,4-dimethyl-2-(2-lithiophenylpropan-2-yl)oxazoline (LiPhCMe2Ox), salt (FeBr2) metathesis proved uncompetitive with oxazoline ring-opening, as exhibited by [{Κ-N,O-C6H4CMe 2C=NCMe2CH2(μ-O)-}BrFe{Κ-N,O-C 6H4CMe2C=NCMe2CH2(μ-O) -}FeBr]Li {Κ-N,O-C6H4CMe2-C=NCMe 2CH2(μ-O)-}(DME) (5-Fe2Li). Metatheses utilizing (PhCMe2Ox)2Zn, prepared from LiPhCMe 2Ox and ZnCl2, gave structurally characterized dichromium, i.e., [{Κ-C,N-(o-C6H4)CMe2 (COCH 2CMe2N)}Cr]2(μ-Cl)2 (6 2), and iron, i.e., {Κ-C,N-{(o-C6H 4)CMe2(COCH2CMe2N)}Fe(py)Cl (7) products. Bis-aryloxazoline metal complexes proved difficult to prepare, with {Κ-C,N-(o-C6H4)CMe2(COCH 2CMe2N)}2M (M = Ni, 9) the only clear example, although NMR evidence exists for M = Fe (8).

Remote C-H bond functionalization reveals the distance-dependent isotope effect

Iodination of remote aryl C-H bonds has been achieved using palladium acetate as the catalyst and iodoacetate (IOAc) as the oxidant. Systematic kinetic isotope studies imply a mechanistic regime shift as the number of bonds separating the directing heteroatom and the target C-H bond increases. Both isotope and electronic effects observed in remote C-H bond activation are consistent with an electrophilic palladation pathway in which the initial palladation is slower than the C-H bond cleavage.

Palladium-catalyzed alkylation of aryl C-H bonds with sp3 organotin reagents using benzoquinone as a crucial promoter

The combination of directed C-H activation, batch-wise addition of tetraalkyltin reagents, and rate enhancement by benzoquinone and microwave irradiation provides a promising strategy for the direct coupling of C-H bonds with organometallic reagents. A variety of tetraalkyltins were coupled to C-H bonds to give the alkylated products in good yields by using 5 mol % Pd(OAc)2 as the catalyst. Benzoquinone was shown to be essential for the C-H activation when substrates containing non-π-conjugated chelating groups are used. Monitoring the formation and reductive elimination of the Pd(Ar)(Me)L2 complex also revealed that benzoquinone promotes the reductive elimination step. Microwave irradiation enhances the reaction rate drastically. The versatility of this protocol was demonstrated by using substrates containing either oxazoline or pyridine as directing groups. Copyright