618-34-8Relevant academic research and scientific papers
A practical synthetic method for vinyl chlorides and vinyl bromides from ketones via the corresponding vinyl phosphate intermediates
Kamei, Katsuhide,Maeda, Noriko,Tatsuoka, Toshio
, p. 229 - 232 (2005)
A new synthetic method for the preparation of vinyl chlorides and vinyl bromides from acyclic and cyclic ketones is described. Vinyl halides are practically obtained from the corresponding vinyl phosphate intermediates with triphenylphosphine dihalide.
A novel titanium tetrahalide-mediated carbon-carbon bond-forming reaction: Regioselective synthesis of substituted (E,Z)-1,5-dihalo-1,4-dienes
Kabalka, George W.,Wu, Zhongzhi,Ju, Yuhong
, p. 3415 - 3417 (2002)
(matrix presented) Reactions of aldehydes with 2 equiv of alkyne in the presence of TiX4 (X = Cl, Br) regioselectively generated 1,5-dihalo-1,4-dienes in moderate to good yields with high (E,Z)-stereoselectivity.
Synthesis of Unsymmetrical 1,4-Dicarbonyl Compounds by Photocatalytic Oxidative Radical Additions
Dong, Ya,Li, Ruining,Zhou, Junliang,Sun, Zhankui
supporting information, p. 6387 - 6390 (2021/08/23)
Herein we report a photocatalytic oxidative radical addition reaction for the synthesis of unsymmetrical 1,4-dicarbonyl compounds. This reaction utilizes a desulfurization process to generate electrophilic radicals, which add to α-halogenated alkenes and undergo further oxidation to deliver 1,4-dicarbonyl compounds. This mild and highly efficient method provides a valuable alternative to known strategies.
Method for preparing vinyl chloride compound by utilizing phosgene
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Paragraph 0097-0109, (2020/06/20)
The invention relates to a method for preparing a vinyl chloride compound by using phosgene. The method comprises the following steps: dropwise adding an organic solvent solution of phosgene into an organic solvent solution containing quaternary phosphoni
Chloride-tolerant gold(I)-catalyzed regioselective hydrochlorination of alkynes
Ebule, Rene,Liang, Shengzong,Hammond, Gerald B.,Xu, Bo
, p. 6798 - 6801 (2017/11/09)
We have developed a highly regioselective homogeneous gold(I)-catalyzed anti-hydrochlorination of unactivated alkynes at room temperature. We have overcome the incompatibility between conventional cationic gold catalysts and chloride by using a hydrogen-b
A Chlorinating Reagent Yields Vinyl Chlorides with High Regioselectivity under Heterogeneous Gold Catalysis
Liang, Shengzong,Ebule, Rene,Hammond, Gerald B.,Xu, Bo
supporting information, p. 4524 - 4527 (2017/09/11)
A novel chlorinating reagent with a high concentration of HCl has enabled the highly regioselective hydrochlorination of unactivated alkynes using a commercial nanogold catalyst. No overchlorination or hydration products were formed, and various functional groups were tolerated. This hydrochlorination method could be conducted under open air.
Catalytic Enantioselective Synthesis of Halocyclopropanes
Pons, Amandine,Ivashkin, Pavel,Poisson, Thomas,Charette, André B.,Pannecoucke, Xavier,Jubault, Philippe
supporting information, p. 6239 - 6242 (2016/05/02)
A catalytic asymmetric synthesis of halocyclopropanes is described. The developed method is based on a carbenoid cyclopropanation of 2-haloalkenes with tert-butyl α-cyano-α-diazoacetate using a chiral rhodium catalyst that permits access to a broad range
Catalyst-free hydrochlorination protocol for terminal arylalkynes with hydrogen chloride
Xu, Cai-Xia,Ma, Cun-Hua,Xiao, Fu-Rong,Chen, Hong-Wei,Dai, Bin
supporting information, p. 1683 - 1685 (2016/11/12)
We present a simple and straightforward protocol for hydrochlorination of terminal arylalkynes to vinyl chlorides using hydrogen chloride under mild reaction conditions. This protocol does not involve any metal catalysts or additives. It is simple, inexpensive, and easy to prepare, and exhibits good reaction activity. The hydrochlorination proceeds smoothly to yield unique regioselective products via the Markovnikov addition rule.
Synthesis of Vinyl Chlorides via Triphosgene-Pyridine Activation of Ketones
Saputra, Mirza A.,Ngo, Ly,Kartika, Rendy
, p. 8815 - 8820 (2015/09/15)
Herein, we describe a mild method to prepare aliphatic and aromatic vinyl chlorides from their corresponding ketones via triphosgene-pyridine activation in dichloromethane at reflux. The mechanism of this reaction is proposed to involve formation of a put
Selective Ruthenium-Catalyzed Hydrochlorination of Alkynes: One-Step Synthesis of Vinylchlorides
Dérien, Sylvie,Klein, Hubert,Bruneau, Christian
supporting information, p. 12112 - 12115 (2015/10/12)
An unprecedented ruthenium-catalyzed direct and selective alkyne hydrochlorination is reported and leads to vinylchlorides in excellent yields with atom economy. The reaction proceeds at room temperature from terminal alkynes and provides a variety of chloroalkenes. Only the regioisomer resulting from the formal Markovnikov addition is selectively formed. Mechanistic studies show the stereoselective syn addition of HCl to alkynes at room temperature and suggest a chloro hydrido RuIV species as a key intermediate of the reaction.
