83438-57-7Relevant articles and documents
Visible Light-Induced Room-Temperature Heck Reaction of Functionalized Alkyl Halides with Vinyl Arenes/Heteroarenes
Kurandina, Daria,Parasram, Marvin,Gevorgyan, Vladimir
supporting information, p. 14212 - 14216 (2017/10/13)
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.
Pd-Catalyzed C(sp3)-C(sp2) cross-coupling of Y(CH2SiMe3)3(THF)2 with vinyl bromides and triflates
Cai, Guilong,Zhou, Zhibing,Wu, Wenchao,Yao, Bo,Zhang, Shaowen,Li, Xiaofang
supporting information, p. 8702 - 8706 (2016/10/03)
Pd-Catalyzed C(sp3)-C(sp2) cross-coupling of Y(CH2SiMe3)3(THF)2 with vinyl bromides and triflates has been developed for efficient synthesis of various allyltrimethylsilanes. The cross-coupling reaction was conducted at room temperature with low catalyst loading of either Pd(PPh3)4 or Pd(PPh3)2Cl2, and exhibited high efficiency and a broad substrate scope. In combination with the cross-coupling by the Lewis-acid catalyzed Hosomi-Sakurai reaction, a novel three-component one-pot cascade reaction was then accomplished to deliver homoallylic alcohols and ethers with high regioselectivity and diastereoselectivity. The three-component reaction defined the yttrium complex as a novel one-carbon synthon, which could either trigger bifunctionalization of alkenes or link two electrophiles and would find applications in organic synthesis.
Nickel catalyzed dealkoxylative Csp2-Csp3 cross coupling reactions - Stereospecific synthesis of allylsilanes from enol ethers
Guo, Lin,Leiendecker, Matthias,Hsiao, Chien-Chi,Baumann, Christoph,Rueping, Magnus
supporting information, p. 1937 - 1940 (2015/02/05)
The application of cyclic and acyclic enol ethers as electrophiles in cross coupling reactions offers new possibilities for the preparation of functional compounds. A novel nickel catalyzed dealkoxylative cross coupling reaction allows access to structurally diverse allylsilanes and alcohol derivatives with high stereospecificity and in good yields under mild reaction conditions directly from the corresponding enol ethers.
Regioselective Synthesis of Allyltrimethylsilanes from Allylic Halides and Allylic Sulfonates. Application to the Synthesis of 2,3-Bis(trimethylsilyl)alk-1-enes
Smith, Janice Gorzynski,Drozda, Susan E.,Petraglia, Susan P.,Quinn, Nina R.,Rice, Elizabeth M.,et al.
, p. 4112 - 4120 (2007/10/02)
The preparation of allyltrimethylsilanes by regioselective pathways is described.Treatment of (E)-1-chloro-2-alkenes with a reagent prepared from 1 equiv each of trimethylsilyllithium and copper(I) iodide in hexamethylphosphoramide to presumably form a (trimethylsilyl)copper reagent affords 3-(trimethylsilyl)-1-alkenes in good to excellent yields with a high regioselectivity.Treatment of these same 1-chloro-2-alkenes with (trimethylsilyl)lithium alone without added copper(I) iodide yields only (E)-1-(trimethylsilyl)-2-alkenes.A single allylic halide thus yields two regioisomeric allyltrimethylsilanes by proper choice of reaction conditions.The reaction of a variety of allylic sulfonates with (trimethylsilyl)copper has also been investigated.The mesylates of 2 deg and 3 deg allylic alcohols yield mixtures of isomeric allyltrimethylsilanes in which the 1-(trimethylsilyl)-2-alkenes predominate.With geraniol, the mesylate was prepared in situ and allowed to react with (trimethylsilyl)copper to afford two isomeric allyltrimethylsilanes in which the 3-(trimethylsilyl)-1-alkene predominates.Finally, these reactions have also been used to prepare a variety of 2,3-bis(trimethylsilyl)alk-1-enes, a class of unsaturated organosilanes which has received little attention in the literature.
PRACTICAL SYNTHESES OF ALLYLSILANES FROM 1-BENZENESULFONYL-2-TRIMETHYLSILYLETHANE
Hsiao, C-N.,Shechter, H.
, p. 1963 - 1966 (2007/10/02)
The methanesulfonates of the adducts of aldehydes and ketones with 1-(1-benzenesulfonyl-2-trimethylsilyl)ethyllithium are converted by sodium-amalgam to allylsilanes.
