29268-75-5Relevant academic research and scientific papers
One-pot, oxidative and selective conversion of benzylic silyl and tetrahydropyranyl ethers to gem-dichlorides using trichloroisocyanuric acid and triphenylphosphine as an efficient and neutral system
Khadem Moghaddam, Roqayeh,Aghapour, Ghasem
, p. 398 - 406 (2020/11/19)
A one-pot and oxidative method is described for the first time for the conversion of benzylic trimethylsilyl (TMS) and tetrahydropyranyl (THP) ethers to gem-dichlorides using trichloroisocyanuric acid (TCCA) and triphenylphosphine (PPh3) in neutral media. Various theses substrates containing electron withdrawing or donating groups can be efficiently converted to their corresponding gem-dichlorides in good to excellent yields. The present method shows a high degree of chemoselectivity, and due to its one-pot nature is in accordance with green chemistry.
Formamide Catalysis Facilitates the Transformation of Aldehydes into Geminal Dichlorides
Huy, Peter Helmut
supporting information, p. 2474 - 2483 (2019/06/08)
Herein, a novel method for the transformation of aldehydes into geminal dichlorides based on phthaloyl chloride as reagent and N -formylpyrrolidine as Lewis base catalyst is disclosed. Given the mild reaction conditions, the current protocol is distinguished by high levels of functional group compatibility and scalability and is operationally simple. The in situ formation of a Vilsmeier Haack reagent type intermediate is likely to be essential for this organocatalytic nucleophilic substitution reaction.
One-pot, selective and mild conversion of benzylic alcohols to gem -dichlorides using chlorodiphenylphosphine and 2,3-dichloro-5,6-dicyanobenzoquinone as a new and neutral system
Aghapour, Ghasem,Mohamadian, Samaneh
, p. 520 - 527 (2015/05/20)
A mild and one-pot conversion of benzylic alcohols to their corresponding gem-dichlorides is reported for the first time using chlorodiphenylphosphine (ClPPh2) and 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) in dichloromethane under neutral conditions and at room temperature. The present method can be efficiently used for preparation of gem-dichlorides even in the presence of some other functional groups with excellent chemoselectivity.
Phosphorus(V)-catalyzed deoxydichlorination reactions of aldehydes
An, Jie,Tang, Xiaoping,Moore, Joshua,Lewis, William,Denton, Ross M.
, p. 8769 - 8776 (2013/09/23)
A phosphine oxide-catalyzed conversion of aldehydes into 1,1-dichlorides is reported. The reaction proceeds via a phosphorus(V)-catalysis manifold in which phosphine oxide turnover is achieved using oxalyl chloride as a consumable reagent. The new method is applicable to a range of aldehydes and, in combination with palladium-catalyzed reductive dimerization, gives rise to a new catalytic approach to the synthesis of stilbenes and a short formal synthesis of resveratrol.
Z-selective copper-catalyzed asymmetric allylic alkylation with grignard reagents
Giannerini, Massimo,Fananas-Mastral, Martin,Feringa, Ben L.
supporting information; experimental part, p. 4108 - 4111 (2012/04/10)
Allylic gem-dichlorides undergo regio- and enanantioselective (er up to 99:1) copper-catalyzed allylic alkylation with Grignard reagents affording chiral Z-vinyl chlorides. This highly versatile class of synthons can be subjected to Suzuki cross coupling affording optically active Z-alkenes and 1,3-cis,trans dienes.
Hexamethylphosphoramide Catalyzed Conversion of Carbonyl Compounds into geminal-Dichlorides with Thionyl Chloride
Khurana, J. M.,Mehta, Sanjay
, p. 1128 (2007/10/02)
α, β-Unsaturated and aromatic aldehydes can be converted into geminal-dichlorides quantitatively by reaction with thionyl chloride in the presence of catalytic amounts of hexamethylphosphoramide at room temperature
