27059-40-1Relevant articles and documents
Indium-Catalyzed Formal Carbon-Halogen Bond Insertion: Synthesis of α-Halo-α,α-disubstituted Esters from Benzylic Halides and Diazo Esters
Nishimoto, Yoshihiro,Wang, Fei,Yasuda, Makoto
, p. 1706 - 1710 (2022/03/14)
One-carbon-unit insertion into carbon-halogen (C-X) bonds accompanied by the formation of a new C-X bond and carbon-chain elongation is a powerful synthetic method of complex organohalides. Herein, we developed an indium trihalide catalyzed formal insertion of diazo esters into a C-X (X = Cl, Br, I) bond. In the present system, the reactions of α-aryl diazo esters with benzylic chlorides, bromides, and iodides yielded α-chloro, α-bromo, and α-iodo esters, respectively.
Iron-catalysed enantioconvergent Suzuki-Miyaura cross-coupling to afford enantioenriched 1,1-diarylalkanes
Tyrol, Chet C.,Yone, Nang S.,Gallin, Connor F.,Byers, Jeffery A.
supporting information, p. 14661 - 14664 (2020/12/02)
The first stereoconvergent Suzuki-Miyaura cross-coupling reaction was developed to afford enantioenriched 1,1-diarylalkanes. An iron-based complex containing a chiral cyanobis(oxazoline) ligand framework was best to obtain enantioenriched 1,1-diarylalkanes from cross-coupling reactions between unactivated aryl boronic esters and benzylic chlorides. Enhanced yields were obtained when 1,3,5-trimethoxybenzene was used as an additive, which is hypothesized to extend the lifetime of the iron-based catalyst. Exceptional enantioselectivities were obtained with challenging ortho-substituted benzylic chlorides. This journal is
α-Diimine-Niobium Complex-Catalyzed Deoxychlorination of Benzyl Ethers with Silicon Tetrachloride
Parker, Bernard F.,Hosoya, Hiromu,Arnold, John,Tsurugi, Hayato,Mashima, Kazushi
supporting information, p. 12825 - 12831 (2019/10/19)
α-Diimine niobium complexes serve as catalysts for deoxygenation of benzyl ethers by silicon tetrachloride (SiCl4) to cleanly give two equivalents of the corresponding benzyl chlorides, where SiCl4 has the dual function of oxygen scavenger and chloride source with the formation of a silyl ether or silica as the only byproduct. The reaction mechanism has two successive trans-etherification steps that are mediated by the niobium catalyst, first forming one equivalent of benzyl chloride along with the corresponding silyl ether intermediate that undergoes the same reaction pathway to give the second equivalent of benzyl chloride and silyl ether.
Ruthenium-Catalyzed Reductive Arylation of N-(2-Pyridinyl)amides with Isopropanol and Arylboronate Esters
Ronson, Thomas O.,Renders, Evelien,Van Steijvoort, Ben F.,Wang, Xubin,Wybon, Clarence C. D.,Prokopcová, Hana,Meerpoel, Lieven,Maes, Bert U. W.
supporting information, p. 482 - 487 (2019/01/04)
A new three-component reductive arylation of amides with stable reactants (iPrOH and arylboronate esters), making use of a 2-pyridinyl (Py) directing group, is described. The N-Py-amide substrates are readily prepared from carboxylic acids and PyNH2, and the resulting N-Py-1-arylalkanamine reaction products are easily transformed into the corresponding chlorides by substitution of the HN-Py group with HCl. The 1-aryl-1-chloroalkane products allow substitution and cross-coupling reactions. Therefore, a general protocol for the transformation of carboxylic acids into a variety of functionalities is obtained. The Py-NH2 by-product can be recycled.
Desulfurative Chlorination of Alkyl Phenyl Sulfides
Canestrari, Daniele,Lancianesi, Stefano,Badiola, Eider,Strinna, Chiara,Ibrahim, Hasim,Adamo, Mauro F. A.
, p. 918 - 921 (2017/02/26)
The chlorination of readily available secondary and tertiary alkyl phenyl sulfides using (dichloroiodo)benzene (PhICl2) is reported. This mild and rapid nucleophilic chlorination is extended to sulfa-Michael derived sulfides, affording elimination-sensitive β-chloro carbonyl and nitro compounds in good yields. The chlorination of enantioenriched benzylic sulfides to the corresponding inverted chlorides proceeds with high stereospecificity, thus providing a formal entry into enantioenriched chloro-Michael adducts. A mechanism implying the formation of a dichloro-λ4-sulfurane intermediate is proposed.
Interpretation of retention indices in gas chromatography for establishing structures of isomeric products of alkylarenes radical chlorination
Zenkevich
, p. 270 - 280 (2007/10/03)
By an example of previously uncharacterized products obtained by alkylarenes radical chlorination was demonstrated that combination of various interpretation methods applied to the retention indices (RI) in the gas chromatography on the standard nonpolar phases (comparison of RI of products and initial compounds, characteristics of succession of the chromatographic elution of the structural isomers with the use of estimation of molecular dynamic parameters, application of the additive schemes to RI calculation, and using of structural analogy CH3?Cl for testing the results obtained) permitted unambiguous identification of the structure even without data of mass spectrometry.
Scope and Limitations of Aliphatic Friedel-Crafts Alkylations. Lewis Acid Catalyzed Addition Reactions of Alkyl Chlorides to Carbon-Carbon Double Bonds
Mayr, Herbert,Striepe, Wilhelm
, p. 1159 - 1165 (2007/10/02)
Lewis acid catalyzed addition reactions of alkyl halides 1 with unsaturated hydrocarbons 2 have been studied. 1:1 addition products 3 are formed if the addends 1 dissociate faster than the corresponding products 3; otherwise, polymerization of 2 takes place.For reaction conditions under which 1 and 3 exist mainly undissociated, solvolysis constants of model compounds can be used to predict the outcome of any such addition reactions if systems with considerable steric hindrance are excluded.
Reactions of Difluoridichloromethane with Hydrocarbons
Schmidt, H.,Burtzlaff, Ch.,Masuhr, H.',Ohl, J.,Pehle, W.,et al.
, p. 751 - 760 (2007/10/02)
The reaction of difluoridichloromethane with different hydrocarbons between 150 deg C and 250 deg C yields the CFCl2-substituted hydrocarbons.Beside it the corresponding chlorides are formed.For the hydrocarbons studied the following sequence of reactivity against difluordichloromethane was found: n-paraffins isoparaffins ca. cycloparaffins alkylaromatics olefines.
