1229-75-0Relevant academic research and scientific papers
Microwave-assisted periselective annulation of triarylphosphenes with aldehydes and ketones
Du, Changle,Fu, Xingyang,Fu, Zhicheng,Luo, Yun,Xu, Jiaxi
, p. 9526 - 9537 (2020/12/15)
The reaction of diazo(aryl)methyl(diaryl)phosphine oxides with aldehydes and ketones generates benzo-δ-phosphinolactones in low to good yields with 1,1-diarylalk-1-enes as byproducts under microwave irradiation. Diazo(aryl)methyl(diaryl)phosphine oxides first undergo a Wolff rearrangement to form diaryl(aryl)phosphenes, which further react with aldehydes and ketones to afford benzo-δ-phosphinolactones and β-phosphinolactones. The latter are unstable under heating and fragment into the corresponding 1,1-diarylalk-1-enes and arylphosphine dioxides under reaction conditions. The arylphosphine dioxides become arylphosphonic acids during workup. The periselectivity in the annulation shows that the reaction of diaryl(aryl)phosphenes with most aldehydes and ketones favors phosphene phenyl participation in (4 + 2) annulation(2 + 2) annulation. This journal is
Electrochemical Aziridination by Alkene Activation Using a Sulfamate as the Nitrogen Source
Li, Jin,Huang, Wenhao,Chen, Jingzhi,He, Lingfeng,Cheng, Xu,Li, Guigen
supporting information, p. 5695 - 5698 (2018/04/30)
The first direct aziridination of triaryl-substituted alkenes was achieved by means of an electrochemical process that could extend to multisubstituted styrenes. Specifically, hexafluoroisopropanol sulfamate was used as a nucleophilic nitrogen source. Mechanistic experiments suggest that this electrochemical process proceeds by stepwise formation of two C?N bonds through reactions between cationic carbon species and the sulfamate.
Reduction of titanocene dichloride with dysprosium: Access to a stable titanocene(II) equivalent for phosphite-free Takeda carbonyl olefination
Bousrez,Déchamps,Vasse,Jaroschik
supporting information, p. 9359 - 9362 (2015/06/16)
The reduction of titanocene dichloride with dysprosium yields a new titanocene(ii) equivalent without the need for further stabilising ligands. This reagent can be employed in combination with dithioacetals for the olefination of different carbonyl groups and allows for a simplified all-in-one procedure.
One-pot synthesis of 1-iodoalkynes and trisubstituted alkenes from benzylic and allylic bromides
Pelletier, Guillaume,Lie, Sharon,Mousseau, James J.,Charette, Andre B.
supporting information, p. 5464 - 5467,4 (2020/10/15)
1-Iodoalkynes are formed in moderate to high yields from readily accessible benzylic and allylic alkyl bromides by a one-pot homologation/double elimination procedure with iodoform (CHI3). The developed conditions include facile purification and avoid the use of an excess of triphenylphosphine (PPh3), as described in classical Corey-Fuchs iodoalkynylation conditions. Replacing CHI3 with CHI2Cl allows the isolation of the corresponding gem-(Z)-chloro-(E)-iodoalkene in good yield and stereoselectivity. Moreover, the use of benzhydryl bromides as nucleophiles enables the synthesis of trisubstituted alkenes under similar reaction conditions.
Direct arylation of alkenes with aryl iodides/bromides through an organocatalytic radical process
Sun, Chang-Liang,Gu, Yi-Fan,Wang, Bin,Shi, Zhang-Jie
supporting information; experimental part, p. 10844 - 10847 (2011/10/31)
A radical addition: A KOtBu-complex-promoted radical arylation of polysubstituted alkenes with aryl iodides/bromides proceeds in high efficiency (see scheme). Benzofuran derivatives are also produced starting from readily available allyl 2-iodophenyl ethers. Copyright
Structural optimization of enantiopure 2-cyclialkylamino-2-aryl-1,1- diphenylethanols as catalytic ligands for enantioselective additions to aldehydes
Rodriguez-Escrich, Sergi,Reddy, Katamreddy Subba,Jimeno, Ciril,Colet, Gisela,Rodriguez-Escrich, Carles,Sola, Lluis,Vidal-Ferran, Anton,Pericas, Miquel A.
, p. 5340 - 5353 (2008/12/20)
(Chemical Equation Presented) The structural optimization of a family of modular, enantiopure β-amino alcohol ligands with a common 2-amino-2-aryl-1,1-diphenylethanol skeleton, whose stereogenicity was introduced through the Jacobsen epoxidation of 1,1-diphenyl-2-arylethylenes, has led to the identification of a small set of optimal catalysts with enhanced activity and enantioselectivity in the addition of alkylzinc and arylzinc reagents to aldehydes. Criteria for the discrimination between apparently analogous, highly enantioselective ligands are proposed.
Synthesis of heavily substituted 1,2-amino alcohols in enantiomerically pure form
Garcia-Delgado, Noemi,Reddy, Katamreddy Subba,Sola, Lluis,Riera, Antoni,Pericas, Miquel A.,Verdaguer, Xavier
, p. 7426 - 7428 (2007/10/03)
A simple and convenient methodology for the preparation of optically pure 2-amino-2-aryl-1,1-diphenylethanols is presented. Allylamine was found to produce the ring-opening of triaryloxiranes in a regioselective and a stereospecific fashion. Removal of the allyl protecting group provided the free 1,2-amino alcohols in enantiomerically pure form.
Synthesis of polysubstituted alkenes by Heck vinylation or Suzuki cross-coupling reactions in the presence of a tetraphosphane-palladium catalyst
Berthiol, Florian,Doucet, Henri,Santelli, Maurice
, p. 1091 - 1096 (2007/10/03)
Through the use of [PdCl(C3H5)]2/cis,cis,cis-1,2,3, 4-tetrakis[(diphenylphosphanyl)methyl]cyclopentane as a catalyst, a range of vinyl bromides undergo Suzuki cross-couplings with arylboronic acids in good yields. Furthermore, the catalyst can be used at low loadings, even for reactions of sterically hindered substrates. Mediated by this catalyst, stilbene and 1,1-diphenylethylene undergo Heck reactions with aryl halides to give triarylethylene derivatives. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
