110166-76-2Relevant academic research and scientific papers
Synthesis and Photochemical Application of Hydrofluoroolefin (HFO) Based Fluoroalkyl Building Block
Varga, Bálint,Tóth, Balázs L.,Béke, Ferenc,Csenki, János T.,Kotschy, András,Novák, Zoltán
supporting information, p. 4925 - 4929 (2021/07/01)
A novel fluoroalkyl iodide was synthesized on multigram scale from refrigerant gas HFO-1234yf as cheap industrial starting material in a simple, solvent-free, and easily scalable process. We demonstrated its applicability in a metal-free photocatalytic ATRA reaction to synthesize valuable fluoroalkylated vinyl iodides and proved the straightforward transformability of the products in cross-coupling chemistry to obtain conjugated systems.
Enantioselective Functionalization of Difluorocyclopropenes Catalyzed by Chiral Copper Complexes: Proposal for Chiral gem-Dimethyl and tert-Butyl Analogues
Sekine, Keisuke,Ushiyama, Aina,Endo, Yu,Mikami, Koichi
supporting information, p. 7916 - 7924 (2020/07/16)
The highly enantioselective copper/chiral phosphine-catalyzed hydro-, bora-, and carbo-metalations of difluorocyclopropenes with PHMS [H-Si], H-BPin, (BPin)2, and (CH3)2Zn [Zn-Me] are shown to regiodivergently afford highly enantioenriched and functionalized difluorocyclopropanes. These examples can be viewed as the first successful syntheses of "chiral"gem-dimethyl and tert-butyl analogues.
Copper-Catalyzed Ring Opening of [1.1.1]Propellane with Alkynes: Synthesis of Exocyclic Allenic Cyclobutanes
Lasányi, Dániel,Tolnai, Gergely L.
supporting information, p. 10057 - 10062 (2019/12/24)
Despite the long history and interesting properties of propellanes, these compounds still have tremendous potential to be exploited in synthetic organic chemistry. Herein we disclose an experimentally simple procedure to achieve cyclobutane-containing allenes and alkynes through a copper-catalyzed ring opening of [1.1.1]propellane and subsequent reaction with ethynes.
Cobalt(II)-based Metalloradical Activation of 2-(Diazomethyl)pyridines for Radical Transannulation and Cyclopropanation
Roy, Satyajit,Das, Sandip Kumar,Chattopadhyay, Buddhadeb
supporting information, p. 2238 - 2243 (2018/02/19)
A new catalytic method for the denitrogenative transannulation/cyclopropanation of in-situ-generated 2-(diazomethyl)pyridines is described using a cobalt-catalyzed radical-activation mechanism. The method takes advantage of the inherent properties of a CoIII-carbene radical intermediate and is the first report of denitrogenative transannulation/cyclopropanation by a radical-activation mechanism, which is supported by various control experiments. The synthetic benefits of the metalloradical approach are showcased with a short total synthesis of (±)-monomorine.
Hydroiodination-Triggered Cascade Reaction with I2/PPh3/H2O: Metal-Free Access to 3-Substituted Phthalides from 2-Alkynylbenzoates
Kawaguchi, Shin-Ichi,Nakamura, Kentaro,Yamaguchi, Kotaro,Sato, Yuki,Gonda, Yuhei,Nishioka, Masaaki,Sonoda, Motohiro,Nomoto, Akihiro,Ogawa, Akiya
supporting information, p. 5343 - 5346 (2017/09/06)
Phthalide is an important scaffold found in several biologically active compounds. Therefore, effective methods for the synthesis of phthalides are strongly desired. Herein, we describe the metal-free synthesis of 3-substituted phthalides by the reductive hydroiodination of 2-alkynylbenzoates through an I2/PPh3/H2O-triggered cascade reaction. A variety of 3-substituted phthalides were synthesized in excellent yields by a one-pot reaction involving four processes: desilylation, hydroiodination, cyclization, and reduction.
