1833-42-7Relevant academic research and scientific papers
para-Selective Benzylation of Aryl Iodides by the in situ Preparation of ArIF2: a Hypervalent Iodine-Guided Electrophilic Substitution
Chaudhry, Azka,Hyatt, I. F. Dempsey,Im, Haram,Jones, Taro J.,Noorollah, Jennifer,Siddiqi, Fatima,Singh, Nirvanie,Spatola, Nicholas R.
supporting information, (2020/04/16)
Hypervalent iodine-guided electrophilic substitution (HIGES) was described previously for the para-selective benzylation of aryl-λ3-iodane diacetates. One drawback of the method was the synthesis and isolation of hypervalent iodine starting mat
Murahashi Cross-Coupling at ?78 °C: A One-Pot Procedure for Sequential C?C/C?C, C?C/C?N, and C?C/C?S Cross-Coupling of Bromo-Chloro-Arenes
Sinha, Narayan,Heijnen, Dorus,Feringa, Ben L.,Organ, Michael G.
supporting information, p. 9180 - 9184 (2019/07/04)
The coupling of organolithium reagents, including strongly hindered examples, at cryogenic temperatures (as low as ?78 °C) has been achieved with high-reactivity Pd-NHC catalysts. A temperature-dependent chemoselectivity trigger has been developed for the selective coupling of aryl bromides in the presence of chlorides. Building on this, a one-pot, sequential coupling strategy is presented for the rapid construction of advanced building blocks. Importantly, one-shot addition of alkyllithium compounds to Pd cross-coupling reactions has been achieved, eliminating the need for slow addition by syringe pump.
Modular Functionalization of Arenes in a Triply Selective Sequence: Rapid C(sp2) and C(sp3) Coupling of C?Br, C?OTf, and C?Cl Bonds Enabled by a Single Palladium(I) Dimer
Keaveney, Sinead T.,Kundu, Gourab,Schoenebeck, Franziska
, p. 12573 - 12577 (2018/09/18)
Full control over multiple competing coupling sites would enable straightforward access to densely functionalized compound libraries. Historically, the site selection in Pd0-catalyzed functionalizations of poly(pseudo)halogenated arenes has been unpredictable, being dependent on the employed catalyst, the reaction conditions, and the substrate itself. Building on our previous report of C?Br-selective functionalization in the presence of C?OTf and C?Cl bonds, we herein complete the sequence and demonstrate the first general arylations and alkylations of C?OTf bonds (in I dimer. This allowed the realization of the first general and triply selective sequential C?C coupling (in 2D and 3D space) of C?Br followed by C?OTf and then C?Cl bonds.
Intramolecular SN′-type aromatic substitution of benzylic carbonates at their para-position
Ueno, Satoshi,Komiya, Sadakazu,Tanaka, Takeshi,Kuwano, Ryoichi
supporting information; experimental part, p. 338 - 341 (2012/03/10)
The benzylic carbonates, which connect with an active methine through an o-phenylene tether at their meta-position, are cyclized by Pd(η3- C3H5)Cp-S-Phos catalyst, yielding 3-methyl-9,10- dihydrophenanthrenes. In the catal
α,n-didehydrotoluenes by photoactivation of (chlorobenzyl) trimethylsilanes: An alternative to enyne-allenes cyclization
Protti, Stefano,Ravelli, Davide,Mannucci, Barbara,Albini, Angelo,Fagnoni, Maurizio
supporting information; experimental part, p. 8577 - 8580 (2012/09/22)
Doubly radical: A novel entry to ?,n-didehydrotoluene (DHT) diradicals is disclosed and proceeds through the photochemical activation of (chlorobenzyl)trimethylsilanes with chloride loss and elimination of the SiMe3+ group (see scheme). The products formed in solution are indicative of the intermediacy of the three isomers of the ?,n-DHT
Model studies of the stereoelectronic effect in Rh(II) mediated carbenoid C-H insertion reactions
Wangt, Peng,Adams, Julian
, p. 3296 - 3305 (2007/10/02)
Electronic effects of rhodium(II) catalyzed intramolecular C-H insertion reactions of 1-methyl-1-(diazoacetyl)-cyclohexane derivatives 4a-i were studied. The C-3 H/C-5 H insertion ratio is modulated by the electron donating or withdrawing capacity of the functional groups at C-3 and C-5. The general finding was that electron donating groups α to the C-H bond in question promote the insertion reaction. As well, we found that the ligands on the catalyst also affected product ratios. The more stabilized the carbene, i.e. with electron donating ligands, proved to be the more discriminating vis-a-vis the regiochemical outcome. We were also able to demonstrate a deuterium kinetic isotope effect for the insertion reaction symmetrical substrate 4i.
AN ELECTROREDUCTIVE SYNTHESIS OF ALLYLSILANES AND BENZYLSILANES
Shono, Tatsuya,Matsumura, Yoshihiro,Katoh, Susumu,Kise, Naoki
, p. 463 - 466 (2007/10/02)
The electrochemical reduction of benzyl and allyl halides carried out in the presence of chlorotrimethylsilane afforded the corresponding benzylsilanes and allylsilanes in satisfactory yields.
