104108-28-3Relevant academic research and scientific papers
Visible Light-Induced Room-Temperature Heck Reaction of Functionalized Alkyl Halides with Vinyl Arenes/Heteroarenes
Kurandina, Daria,Parasram, Marvin,Gevorgyan, Vladimir
, p. 14212 - 14216 (2017)
The first visible light-induced Pd-catalyzed Heck reaction of α-heteroatom substituted alkyl iodides and -bromides with vinyl arenes/heteroarenes has been developed. This transformation efficiently proceeds at room temperature and enables synthesis of valuable functionalized allylic systems, such as allylic silanes, boronates, germanes, stannanes, pivalates, phosphonates, phthalimides, and tosylates from the corresponding α-substituted methyl iodides. Notably, synthesis of the latter substrates failed under existing thermally induced Pd-catalyzed conditions, which highlights the importance of visible light for this transformation.
Addition of allylstannanes to an oxy-stabilized carbenium ion on a 1,7-dioxaspiro[5.5]undecane ring system
Brimble, Margaret A.,Fares, Fares A.,Turner, Peter
, p. 677 - 684 (1998)
The nucleophilic addition of allylstannanes to (2R*,5S*,6S*)-2-acetoxy-5-benzyloxy-1,7-dioxaspiro-[5.5] undecane 1 has been studied. The optimum conditions involve the use of trimethylsilyl trifluoromethanesulfonate in dichloromethane at -78°C. In the exa
Ni-Catalyzed Stannylation of Aryl Esters via C?O Bond Cleavage
Gu, Yiting,Martín, Rúben
supporting information, p. 3187 - 3190 (2017/03/17)
A Ni-catalyzed stannylation of aryl esters with air- and moisture-insensitive silylstannyl reagents via Csp2 ?O cleavage is described. This protocol is characterized by its wide scope, including challenging combinations, thus enabling access to versatile building blocks and orthogonal C?heteroatom bond formations.
Photochemical 1,3-stannyl rearrangement of allylic stannanes
Takuwa, Akio,Kanaue, Takashi,Yamashita, Koichi,Nishigaichi, Yutaka
, p. 1309 - 1314 (2007/10/03)
The photochemical 1,3-stannyl rearrangement of allylic stannanes has been investigated. The photorearrangement of (E)-cinnamyl(triphenyl)stannane is not observed in benzene under anaerobic conditions, while the photoinduced 1,3-stannyl migration takes place in the same solvent under aerobic conditions, or in the presence of organic halides or a radical-trapping agent to give a photoequllibrium mixture of the cinnamylstannane and its branched regioisomer, 1-phenylprop-2-enyl(triphenyl)stannane, with the latter predominating. Cinnamyl(trialkyl)stannanes and their homologues also afford the corresponding branched allylstannanes under similar photochemical conditions. These 1,3-stannyl migrations proceed intramolecularly via cinnamyl π-π* excitation in competition with homolytic (cinnamyl)C-Sn bond fission. In contrast, the 1,3-stannyl migration of crotyl- and prenyl-(tributyl)-stannanes is not efficient, but their triphenyl or dibutylphenyl derivatives undergo the 1,3-rearrangement via excitation of the phenyl group(s) on the tin atom to give a regioisomeric mixture of the starting linear tin compounds and the branched ones with the former predominating.
The Synthesis of Allylstannanes and Vinylstannanes by the Stannyl-cupration of Allenes
Barbero, Asuncion,Cuadrado, Purificacion,Fleming, Ian,Gonzalez, Ana M.,Pulido, Francisco J.
, p. 1030 - 1031 (2007/10/02)
Stannyl-cupration of allenes followed by electrophilic attack gives allyl- and vinylstannanes with a variety of substitution patterns; the regiochemistry of the reaction depends upon the temperature and the nature of the stannyl-cuprate reagent.
