112520-99-7Relevant articles and documents
Practical Stannylation of Allyl Acetates Catalyzed by Nickel with Bu3SnOMe
Komeyama, Kimihiro,Itai, Yuuhei,Takaki, Ken
, p. 9130 - 9134 (2016)
A practical and scalable nickel-catalyzed allylic stannylation of allyl acetates with Bu3SnOMe is described. A variety of acyclic and cyclic allyl acetates, even with base-sensitive moieties, undergoes the stannylation by using NiBr2/4,4′-di-tert-butylbipyridine (dtbpy)/Mn catalyst system to afford highly functionalized allyl stannanes with excellent regioselectivity and yields. Furthermore, the scope of protocol is also extended by the reaction of propargyl acetates, giving rise to propargyl or allenyl stannanes. Additionally, a unique diastereoselectivity using the nickel catalyst different from the palladium was demonstrated for the stannylation of cyclic allyl acetates. In the reaction, inexpensive and stable nickel complexes, abundant reductant (Mn), and atom-economical stannyl source were used.
Indium(III) halide-catalyzed UV-irradiated radical coupling of iodomethylphosphorus compounds with various organostannanes
Suzuki, Itaru,Kiyokawa, Kensuke,Yasuda, Makoto,Baba, Akio
supporting information, p. 1728 - 1731 (2013/06/27)
The first catalytic radical coupling of iodomethylphosphorus compounds was accomplished with allyl-, alkenyl-, and allenylstannanes under UV irradiation in the presence of an indium(III) halide catalyst, for which a transmetalated allylic indium species was confirmed to be an active radical species.
Wurtz-type reductive coupling reaction of allyl bromides and haloorganotins in cosolvent/H2O(NH4Cl)/Zn media as a route to allylstannanes and hexaaryldistannanes
Von Gyldenfeldt, Friederike,Marton, Daniele,Tagliavini, Giuseppe
, p. 906 - 913 (2008/10/08)
Twenty-one allylstannanes have been prepared via a simple Wurtz-type coupling reaction of allyl bromides and R3SnX compounds (R = Me, Et, Pr, Bu, Ph; X = Cl, I, OH), Bu2SnCl2, and (Bu2SnCl)2O in cosolvent/H2O (NH4Cl saturated) media under the mediation of zinc powder. Also R3SnSnR3 compounds (R = Ph, p- and m-Tol) have been prepared via coupling of triaryltin chlorides. The stereochemical course of the reaction between R3SnCl and (C4H7)Br (C4H7 = α-methylallyl, trans- and cis-crotyl) has been extensively studied. Two distinct reactions are involved in the overall process: (i) the coupling reaction, which gives rise stereoselectively to the sole R3SnCH(CH3)CH=CH2 (α-isomer), and (ii) the subsequent isomerization of the α-isomer furnishing mixtures of (α, trans, cis)-isomers. The occurrence of reaction ii depends upon the nature either of the R group or the employed cosolvent. In cyclohexane, the α-isomer is exclusively obtained with R = Bu, while with R = Me, Et, and Pr it is found as a major component in the ternary isomeric mixture. In tetrahydrofuran, 2-propanol, acetonitrile, and pyridine, the isomerization occurs to an extent which depends on the polarity and the coordinating ability of the cosolvent itself. The observed stereoselection has been hypothesized to occur through one-electron transfer from the zinc metal to the (C4H7)Br to form stereoselectively an adsorbed CH2=CHCH(CH3)Br?-Zn?+ radical ion which is trapped by the R3SnCl reactant to form the α-isomer. Similarly, ditin compounds are thought to be formed by interaction of R3SnCl?-Zn?+ radical ions with R3SnCl molecules.
