105337-06-2

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 1888-75-1 isopropyllithium 
• 398453-87-7 (Z)-2-(dimethylphenylsilylmethylene)-3-methylbutanal 
• 4417-80-5 3-methyl-2-methylene-butyraldehyde 
• 591-50-4 iodobenzene 
• 49642-48-0 2,3-dimethylbutanal 
• 92863-39-3 Acetic acid (Z)-2-benzyl-3-methyl-but-1-enyl ester 
• 67468-86-4 1,1-Diacetoxy-2-isopropyl-2-propen 

Relevant academic research and scientific papers

Catalytic C-H Arylation of Aliphatic Aldehydes Enabled by a Transient Ligand

The direct arylation of aliphatic aldehydes has been established via Pd-catalyzed sp3 C-H bond functionalization in the presence of 3-aminopropanoic acids as transient directing groups. The reaction showed excellent functional group compatibility and chemoselectivity in which a predominant preference for functionalizing unactivated β-C-H bonds of methyl groups over others was achieved. In addition, C-H bonds of unactivated secondary sp3 carbons can also be functionalized. The extreme popularity and importance of aliphatic aldehydes would result in broad applications of this novel method in organic chemistry and medicinal sciences.

Fluoride-Promoted Rearrangement of Organo Silicon Compounds: A New Synthesis of 2-(Arylmethyl)aldehydes from 1-Alkynes

A new approach to 2-(arylmethyl)aldehydes 4 based upon a 1,2-anionotropic rearrangement of an aryl group is presented. The synthetic sequence begins with a silylformylation reaction of terminal acetylenes 5 with aryl and heteroaryl silanes 6, followed by treatment of the products (Z)-1 with TBAF. The optimization of the experimental conditions of the fluoride-promoted step is described, together with the synthetic potentialities of the process. A plausible mechanism of the rearrangement reaction is reported that suggests the addition of the fluoride ion to the arylsilicon moiety of β-silylalkenals (Z)-1 and the consequent migration of the aryl group to the adjacent carbon atom. Both aryl and heteroaryl substituents can rearrange without any loss of configuration. Bromofunctionalized substrates undergo an intramolecular reaction that affords exclusively carbacyclobenzyl aldehydes, further enhancing the high synthetic value of this method.

New synthesis of α-benzylaldehydes from 2-(dimethylphenylsilylmethylene)alkanals by fluoride promoted phenyl migration

α-Benzyl aldehydes are prepared from easily available β-silylalkenals and fluoride reagents, under mild experimental conditions; the reaction occurs instantaneously with almost quantitative yields. A plausible mechanism is suggested, which involves a 1,2-

Carbolithiation of an α-amino lithio alkoxide derived from cinnamaldehyde

Cinnamaldehyde adds alkyllithiums on the carbon carbon double bond regioselectively, after protection by the amide of N,N,N' trimethylethanediamine. The benzyllithium reagent thus obtained reacts with electrophiles diastereoselectively.