229333-74-8

Upstream product

• 129217-85-2 trimethyl (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-1-yn-1-yl)silane 
• 591-31-1 3-methoxy-benzaldehyde 
• 42250-04-4 1-(3-methoxyphenyl)-but-3-yn-1-ol 
• 229333-75-9 1-methoxy-3-(4-trimethylsilyl-1-trimethylsiloxybut-3-ynyl)benzene 

Downstream Products

• 35461-93-9 2-(3-Methoxyphenyl)furan 
• 155586-44-0 1-(3-methoxyphenyl)buta-2,3-dien-1-one 

Relevant academic research and scientific papers

Copper-catalyst-controlled site-selective allenylation of ketones and aldehydes with propargyl boronates

A practical and highly site-selective copper-PhBPE-catalyst-controlled allenylation with propargyl boronates has been developed. The methodology has shown to be tolerant of diverse ketones and aldehydes providing the allenyl adducts in high selectivity. T

Synthesis of allenyl ketones and their palladium-catalyzed cycloisomerization/dimerization: Approaching the limits

The preparation of several new allenyl ketones 1a-j and 1o-q is reported. In the case of allenyl ketones with nucleophilic groups in the side-chain like 1k-m, the material polymerized during the purification procedure; with the dialkyl thioether In the product of a Pummerer isomerization, the acetoxymethyl alkyl thioether, 11 was formed. Depending on the route to 1 sometimes either the acetate adducts 8 and the 1-propynyl ketones 9 or the dipropargyl and propargyl allenyl carbinol 14 and 15 were observed as side-products. Good yields of the sensitive aryl γ-halogen-allenyl ketones 23a and 23b were obtained by a new synthetic route, on the other hand the aryl γ-silylallenyl ketone 23c was readily desilylated. Subjecting the new allenyl ketones to the PdCl2(MeCN)2 catalyst provided the 2-substituted furans 2 and the 2,4-disubstituted furans 3 in most cases. The yields and ratios of these products strongly depended on the nature of the groups being present. With the aryl thioether and the γ-halogen allenyl ketones the palladium-catalyzed reaction failed. Detailed structural information about the new products was provided by the X-ray structure analyses of the p-acetamidophenyl propargyl carbinol 6g and the 2-aryl-4-(1-methyl-3-aryl-3-oxo-propen-1-yl furan 3h. Wiley-VCH Verlag GmbH, 1999.