190271-05-7Relevant academic research and scientific papers
Synthesis of alkylbismuths by regiodivergent carbobismuthination of simple alkenes
Nishimoto, Yoshihiro,Takeuchi, Midori,Yasuda, Makoto,Baba, Akio
supporting information, p. 14411 - 14415 (2013/11/06)
Switchable regioselectivity: This study represents the first carbobismuthination of alkenes achieved by the treatment of an alkene with a bismuth halide and a ketene silyl acetal. This eaction is particularly noteworthy in that a change in the type of halogen on a bismuth atom very easily switched the regioselectivity (see scheme). Copyright
Regioselective carboindation of simple alkenes with indium tribromide and ketene silyl acetals
Nishimoto, Yoshihiro,Ueda, Hiroki,Inamoto, Yoshihiro,Yasuda, Makoto,Baba, Akio
supporting information; experimental part, p. 3390 - 3393 (2010/11/04)
(Equation Presented). The regioselective carboindation of simple alkenes with indium tribromide and ketene silyl acetals was accomplished. Various alkenes such as ethylene, 1-alkenes, and cyclic alkenes were applicable for this reaction system. The alkyli
Indium-catalyzed coupling reaction between silyl enolates and alkyl chlorides or alkyl ethers
Nishimoto, Yoshihiro,Saito, Takahiro,Yasuda, Makoto,Baba, Akio
experimental part, p. 5462 - 5471 (2009/12/01)
The coupling reactions of alkyl chlorides with silyl enolates catalyzed by InBr3, and the coupling reactions of alkyl ethers with silyl enolates catalyzed by the combined Lewis acid of InBr3/Me3SiBr are described. In both reaction systems, various types of silyl enolates were used to give corresponding α-alkylated esters, ketones, carboxylic acids, amides, thioesters, and aldehydes.
InCl3-catalyzed cross-coupling of alkyl trimethylsilyl ethers and allylsilanes via an in situ derived combined lewis acid of InCl3 and Me3SiI
Saito, Takahiro,Nishimoto, Yoshihiro,Yasuda, Makoto,Baba, Akio
, p. 8588 - 8590 (2008/02/12)
(Chemical Equation Presented) Direct Csp3-Csp3 coupling of various aliphatic trimethylsilyl ethers and allylsilanes is effectively catalyzed by InCl3 and I2. The transformation is thought to involve an in situ-derived combined Lewis acid of InCl3 and Me3SiI. The reaction can be used for the construction of quaternary-quaternary and quaternary-tertiary carbon-carbon bonds. This system enabled a highly chemoselective coupling to be conducted with a trimethylsilyl ether including an aryl halide moiety. Furthermore, couplings were possible using an alkynyltri-methylsilane and a trimethylsilyl ketene acetal.
Coupling reaction of alkyl chlorides with silyl enolates catalyzed by indium trihalide
Nishimoto, Yoshihiro,Yasuda, Makoto,Baba, Akio
, p. 4931 - 4934 (2008/03/27)
Indium(III) halide catalyzed not only the coupling of alkyl chlorides with silyl enolates derived from esters, ketones, and aldehydes to give a variety of α-alkylated carbonyl compounds but also one-pot, three-component reactions of aldehyde enolate, alkyl chloride, and allylsilane or alkynylsilane.
Magnesium trifluoromethanesulfonimide(triflimide) promoted substitution reactions of allylic and benzylic acetates. Magnesium triflimide as a substitute for magnesium perchlorate.
Grieco, Paul A.,Handy, Scott T.
, p. 2645 - 2648 (2007/10/03)
Magnesium triflimide(10 mol% in methylene chloride) is a convenient catalyst for the nucleophilic substitution of allylic and benzylic acetates, and constitutes a useful alternative to magnesium perchlorate.
SILVER TRIFLATE-PROMOTED COUPLING REACTIONS OF BENZYLIC AND ALLYLIC SULFIDES WITH O-SILYLATED ENOLATES OF KETONES AND ESTERS, A SYNTHESIS OF (+/-)-AR-TURMERONE
Takeda, Kazuyoshi,Torii, Katsumi,Ogura, Haruo
, p. 265 - 266 (2007/10/02)
Reactions of benzylic and allylic sulfides 1 having 5-mercapto-1-phenyl-1H-tetrazolyl group with O-silylated ketone and ester enolates 2 in the presence of silver triflate gave coupling products 3 in good yield. (+/-)-ar-turmerone was synthesized by this
