130460-69-4Relevant academic research and scientific papers
A transition-metal-free Heck-type reaction between alkenes and alkyl iodides enabled by light in water
Liu, Wenbo,Li, Lu,Chen, Zhengwang,Li, Chao-Jun
, p. 6170 - 6174 (2015)
A transition-metal-free coupling protocol between various alkenes and non-activated alkyl iodides has been developed by using photoenergy in water for the first time. Under UV irradiation and basic aqueous conditions, various alkenes efficiently couple with a wide range of non-activated alkyl iodides. A tentative mechanism, which involves an atom transfer radical addition process, for the coupling is proposed.
Photo-induced Decarboxylative Heck-Type Coupling of Unactivated Aliphatic Acids and Terminal Alkenes in the Absence of Sacrificial Hydrogen Acceptors
Cao, Hui,Jiang, Heming,Feng, Hongyu,Kwan, Jeric Mun Chung,Liu, Xiaogang,Wu, Jie
supporting information, p. 16360 - 16367 (2018/11/27)
1,2-Disubstituted alkenes such as vinyl arenes, vinyl silanes, and vinyl boronates are among the most versatile building blocks that can be found in every sector of chemical science. We herein report a noble-metal-free method of accessing such olefins through a photo-induced decarboxylative Heck-type coupling using alkyl carboxylic acids, one of the most ubiquitous building blocks, as the feedstocks. This transformation was achieved in the absence of external oxidants through the synergistic combination of an organo photo-redox catalyst and a cobaloxime catalyst, with H2 and CO2 as the only byproducts. Both control experiments and DFT calculations supported a radical-based mechanism, which eventually led to the development of a selective three-component coupling of aliphatic carboxylic acids, acrylates, and vinyl arenes. More than 90 olefins across a wide range of functionalities were effectively synthesized with this simple protocol.
Silaheterocycles VII; Reactions of Dichloroneopentylsilene with Aldehydes
Auner, Norbert,Seidenschwarz, Claudia
, p. 909 - 920 (2007/10/02)
Dichloroneopentylsilene, Cl2Si=CHCH2But (1), is produced from vinyltrichlorsilane (2) and LiBut in n-pentane at -78 deg C.The reactions of 1 with aromatic aldehydes like benzaldehyde and the 4-methoxy- or 4-fluoro-substituted derivatives, naphthalene-1 and -2- and 9-anthracenecarbaldehyde, furfurale and its S-analogous thiophene carbaldehyde yield 1,2-silaoxetanes by cycloaddition with the carbonyl group.The same is true for the reactions of 1 with pivaline-, butyr- and acetaldehyde.The silaoxetanes cannot be isolated; the formation of dichlorovinylsiloxanes and the olefinic compounds R-CH=CH-CH2But suggests that the cycloreversion of the Si-O four-membered ring competes with an intramolecular isomerization, evidently via formation of a zwitterionic intermediate R-C+HOSiCl2C-HCH2But.The product formation by coupling reactions of lithiated aldehydes and 2 is excluded by performing analogous reactions with the chlorosilanes Me2SiCl(R) (R=Cl, Me, Vi).
