119323-95-4Relevant academic research and scientific papers
Efficient Generation and Synthetic Applications of Alkyl-Substituted Siloxycarbenes: Suppression of Norrish-Type Fragmentations of Alkanoylsilanes by Triplet Energy Transfer
Abe, Manabu,Hagiwara, Chihiro,Ishida, Kento,Kusama, Hiroyuki,Yamazaki, Hokuto
, p. 1249 - 1253 (2020/02/04)
Acylsilanes have been known to undergo isomerization to siloxycarbenes under photoirradiation and the thus generated carbenes can be utilized for various synthetic reactions. But this carbene formation is not necessarily efficient with some alkanoylsilanes because Norrish-type fragmentations compete, which limit the synthetic utility of alkanoylsilanes as carbene precursors. In this study, generation of siloxycarbenes from alkanoylsilanes by visible-light-induced energy transfer was examined by using an Ir complex, [Ir{dF(CF3)ppy}2(dtbpy)]PF6, and was successfully applied to the C?C coupling reactions with boronic esters or aldehydes. This methodology efficiently suppressed undesired Norrish-type reactions and broadened synthetic utility of alkanoylsilanes.
DTBB-Catalysed dilithiation of styrene and its methyl-derivatives: Introduction of two electrophilic reagents
Yus, Miguel,Martínez, Pedro,Guijarro, David
, p. 10119 - 10124 (2007/10/03)
The reaction of styrene and some methyl-substituted styrenes 1 with lithium and a catalytic amount of 4,4′-di-tert-butylbiphenyl (DTBB) in the presence of several electrophiles [Me3SiCl, Me2CO, Et2CO, (CH2)5CO, Pr2CO], in THF, at temperatures ranging from -78 to 0°C, gave, after hydrolysis, products 2 resulting from addition of lithium to the olefinic double bond and successive trapping with the electrophilic reagent. When a carbonyl compound was used as electrophile, mixtures of the monoaddition-reduction compounds 3 and 4 were obtained as by-products, which could be easily separated from the diaddition products 2.
Cleavage of Carbon-Carbon Bonds with High Stereochemical Control. 6. Asymmetric Synthesis of Chiral C-Centered Organosilanes by Haller-Bauer Cleavage of Optically Active, Nonenolizable α-Silyl Phenyl Ketones
Gilday, John P.,Gallucci, Judith C.,Paquette, Leo A.
, p. 1399 - 1408 (2007/10/02)
Sequential alkylation and methylation of l-menthyl ester 10 provides diastereomeric mixtures in which 12 is slighthly enhanced over 13.Conversely, C-silation and alkylation of propionate ester 11 delivers 13 in excess.In either cause, a single chromatogra
