103240-58-0Relevant academic research and scientific papers
Synthesis of conjugated allenes through copper-catalyzed γ-selective and stereospecific coupling between propargylic phosphates and aryl- or alkenylboronates
Yang, Mingyu,Yokokawa, Natsumi,Ohmiya, Hirohisa,Sawamura, Masaya
, p. 816 - 819 (2012/04/05)
A Cu-catalyzed γ-selective coupling reaction between propargylic phosphates and aryl- or alkenylboronates afforded aryl- or alkenyl-conjugated allenes. The reaction showed excellent functional group compatibility in both the propargylic substrates and the boronates. The reaction of an enantioenriched propargylic phosphate proceeded with excellent chirality transfer with 1,3-anti stereochemistry to give axially chiral aryl- and alkenylallenes.
Coupling of n-tosylhydrazones with terminal alkynes catalyzed by copper(i): Synthesis of trisubstituted allenes
Xiao, Qing,Xia, Ying,Li, Huan,Zhang, Yan,Wang, Jianbo
, p. 1114 - 1117 (2011/04/16)
The easy way to allenes: An operationally simple reaction under mild conditions has led to the direct formation of trisubstituted allenes (see scheme; Ts=4-toluenesulfonyl). An unprecedented copper-carbene migratory insertion process seems to take place,
Titanocene(II)-promoted carbonyl alienation utilizing 1, 1-dichloroalk-1-enes
Shono, Tomohiro,Ito, Kenji,Tsubouchi, Akira,Takeda, Takeshi
, p. 2914 - 2916 (2007/10/03)
Treatment of 1,1-dichloroalk-1-enes with Cp2Ti[P(OEt) 3]2 produced organotitanium species, which afford allenes on treatment with aldehydes and ketones The Royal Society of Chemistry 2005.
Palladium-Catalyzed Propargylic vs. Allylic Alkylation
Keinan, Ehud,Bosch, Eric
, p. 4006 - 4016 (2007/10/02)
The relative reactivities of allylic propargylic acetates toward palladium(0)-catalyzed substitution by various nucleophiles were studied bu using three types of model substrates: (a) monofunctional allylic and propargylic acetates with similar structural properties; (b) a bifunctional substrate containing both allyl and propargyl functionalities with no apparent interaction between them; (c) conjugated bifunctional systems, in which the two functionalities may interact with one another.Palladium(0)-catalyzed substitution of propargylic acetates by various carbon nucleophiles was found to be less general than the analogous substitution of allylic acetates.Three modes of reactivity were observed, corresponding to three groups of nucleophiles; (a) stabilized carboanions such as sodium dimethyl malonate, which do not react with propargylic acetates but react readily with allylic acetates; (b) nonstabilized organometallics such as phenylzinc chloride, which react with propargylic and allylic acetates at comparable rates (reaction with the former yielding the allenic product exlusively); and (c) allyl- and allenylstannanes, which react with allylic acetates but do not react with isolated propargylic acetates (except for special cases where the propargylic acetate is also an allylic one).Certain similarities between regioselectivity phenomena in organopalladium and organocopper chemistry are discussed.
