31366-07-1

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 102, p. 6185, 1980 DOI: 10.1021/ja00539a056

InChI:InChI=1/C12H16O/c1-12(2,3)9-11(13)10-7-5-4-6-8-10/h4-8H,9H2,1-3H3

Upstream product

• 13735-81-4 1-styrenyloxytrimethylsilane 
• 507-20-0 tertiary butyl chloride 
• 5650-07-7 3-methyl-1-phenyl-but-2-en-1-one 
• 15681-48-8 lithium dimethylcuprate 
• 1070-83-3 tert-Butylacetic acid 
• 591-51-5 phenyllithium 
• 917-92-0 3,3-Dimethylbut-1-yne 
• 3677-81-4 diphenylboronchloride 
• 5123-17-1 bromodiphenylborane 
• 16717-64-9 1-azidostyrene 
• 594-19-4 tert.-butyl lithium 
• 38442-51-2 tert-butylmercury chloride 
• 34438-71-6 acetophenone enolate 
• 53780-87-3 benzene 

Downstream Products

• 14392-86-0 phenyl 3,3-dimethylbutyrate 
• 62338-03-8 α-neo-pentylbenzyl alcohol 
• 38050-56-5 (3,3-dimethyl-1-phenyl-butylidene)-hydrazinecarboxylic acid ethyl ester 
• 71491-53-7 2-chloro-3,3-dimethyl-1-phenyl-1-butanone 
• 17314-92-0 (3,3-dimethylbutyl)benzene 
• 89549-37-1 N-pivaloyl benzamide 
• 82894-43-7 β,β-dimethyl-α-oximinobutyrophenone 
• 33119-75-4 2-Brom-3,3-dimethyl-1-phenyl-1-butanon 
• 121435-99-2 Z-2-hydroxyimino-1-phenyl-3,3-dimethylbutan-1-one 
• 81788-82-1 (R,R/S,S)-2-(Bromphenylmethyl)-3,3-dimethyl-1-phenyl-1-butanon 
• 104722-24-9 ((Z)-1-Methoxy-3,3-dimethyl-but-1-enyl)-benzene 
• 100649-51-2 ββ-di-isopropyl-α-neopentylstyrene 
• 106149-64-8 2,2,9,9-tetramethyl-4,7-diphenyldec-5-yn-4,7-diol 
• 71527-78-1 2,2-Dichloro-3,3-dimethyl-1-phenyl-butan-1-one 

Relevant academic research and scientific papers

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Herein, we report that merging palladium catalysis with hydrogen atom transfer (HAT) photocatalysis enabled direct arylations and alkenylations of aldehyde C-H bonds, facilitating visible light-catalyzed construction of a variety of ketones. Tetrabutylammonium decatungstate and anthraquinone were found to act as synergistic HAT photocatalysts. Density functional theory calculations suggested a Pd0-PdII-PdIII-PdI-Pd0 pathway and revealed that regeneration of the Pd0 catalyst and the photocatalyst occurs simultaneously in the presence of KHCO3. This regeneration features a low energy barrier, promoting efficient coupling of the palladium catalytic cycle with the photocatalytic cycle. The work reported herein suggests great promise for further applications of HAT photocatalysis in palladium-catalyzed cross-coupling and C-H functionalization reactions to be successful.

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We report herein that a palladium catalyst in combination with a dual phosphine ligand system catalyzes alkylation of silyl enol ether and enamide with a broad scope of tertiary, secondary, and primary alkyl bromides under mild irradiation conditions by blue light-emitting diodes. The reactions effectively deliver α-alkylated ketones and α-alkylated N-acyl ketimines, and it is difficult to prepare the latter by other methods in a stereoselective manner. The α-alkylated N-acyl ketimine products can be further subjected to chiral phosphoric acid-catalyzed asymmetric reduction with Hantzsch ester to deliver chiral N-acyl-protected α-arylated aliphatic amines in high enantioselectivity up to 99% ee, thus providing a method for facile synthesis of chiral α-arylated aliphatic amines, which are of importance in medicinal chemistry research. The N-acetyl ketimine product also reacted smoothly with various types of Grignard reagents to afford sterically bulky N-acetyl α-tertiary amines in high yields. Theoretical studies in combination with experimental investigation provide understanding of the reaction mechanism with respect to the dual ligand effect and the irradiation effect in the catalytic cycle. The reaction is suggested to proceed via a hybrid alkyl Pd(I)-radical species generated by inner-sphere electron transfer of phosphine-coordinated Pd(0) species with alkyl bromide. This intriguing hybrid alkyl Pd(I)-radical species is elucidated by theoretical calculation to be a triplet species coordinated by three phosphine atoms with a distorted tetrahedral geometry, and spin prohibition rather than metal-to-ligand charge transfer contributes to the kinetic stability of the hybrid alkyl Pd(I)-radical species to impede alkyl recombination to generate Pd(II) alkyl intermediate.

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