106137-98-8Relevant articles and documents
Regioselective Silylations of Propargyl and Allyl Pivalates through Ca-Promoted Reductive C(sp3)-O Bond Cleavage
Zhang, Tianyuan,Zheng, Suhua,Kobayashi, Taro,Maekawa, Hirofumi
, p. 7129 - 7133 (2021/09/18)
A practical protocol for the regioselective preparation of 3-phenylpropargylsilanes and 3-phenylallylsilanes in yields of 36-77 and 48-86%, respectively, from readily accessible 3-phenylpropargyl and 1-phenylallyl pivalates was developed through reductive C(sp3)-O bond cleavage. This method represents the first example of the direct application of vastly abundant calcium granules to a reductive coupling reaction. A broad range of propargylsilanes and allylsilanes are simply prepared using easy-to-handle pivalates and chlorotrimethylsilane under mild catalyst-free and additive-free conditions.
Oxoammonium-Mediated Allylsilane–Ether Coupling Reaction
Carlet, Federica,Bertarini, Greta,Broggini, Gianluigi,Pradal, Alexandre,Poli, Giovanni
supporting information, p. 2162 - 2168 (2021/04/02)
A new C(sp3)?H functionalization reaction consisting of the oxidative α-allylation of allyl- and benzyl- methyl ethers has been developed. The C?C coupling could be carried out under mild conditions thanks to the use of cheap and green oxoammonium salts. The scope of the reaction was studied over 27 examples, considering the nature of the substituents on the two coupling partners.
Asymmetric Synthesis Catalyzed by Chiral Ferrocenylphosphine-Transition-Metal Complexes. 3. Preparation of Optically Active Allylsilanes by Palladium-Catalyzed Asymmetric Grignard Cross-Coupling
Hayashi, Tamio,Konishi, Mitsuo,Okamoto, Yasuo,Kabeta, Keiji,Kumada, Makoto
, p. 3772 - 3781 (2007/10/02)
Asymmetric cross-coupling of the - or -Grignard reagent with alkenyl bromides in the presence of a chiral ferrocenylphosphine-palladium complex, dichloroethylamine>palladium(II) (PdCl2), as a catalyst, gave optically active allylsilanes which contain an asymmetric carbon atom directly bonded to the silicon atom, e.g., (R)-3-phenyl-3-(trimethylsilyl)propene (3a) (95percent ee), (R,E)-1-phenyl-1-(trimethylsilyl)-2-butene (3b) (85percent ee), (R,Z)-3b (24percent ee), (R,E)-1,3-diphenyl-3- (trimethylsilyl)propene (3c) (95percent ee), (S,E)-1-phenyl-3-(trimethylsilyl)-1-butene (14c) (71percent ee), (S,Z)-14c (59percent ee), (S,E)-1-phenyl-3-(triethylsilyl)-1-butene (16c) (93percent ee), (S,E)-3-(triethylsilyl)-2-pentene (16b) (85percent ee), (S,E,E)-2-(dimethylphenylsilyl)-3,5-heptadiene (15d) (45percent ee), and 1-cyclopentene (21) (37percent ee).The configuration and enantiomeric purity of the allylsilanes were determined with the aid of stereoselective oxidative cleavage of the carbon-silicon bond in optically active alkylsilanes.