7010-83-5Relevant academic research and scientific papers
Ni/Photoredox-Catalyzed Enantioselective Cross-Electrophile Coupling of Styrene Oxides with Aryl Iodides
Lau, Sii Hong,Borden, Meredith A.,Steiman, Talia J.,Wang, Lucy S.,Parasram, Marvin,Doyle, Abigail G.
supporting information, p. 15873 - 15881 (2021/10/12)
A Ni/photoredox-catalyzed enantioselective reductive coupling of styrene oxides and aryl iodides is reported. This reaction affords access to enantioenriched 2,2-diarylalcohols from racemic epoxides via a stereoconvergent mechanism. Multivariate linear regression (MVLR) analysis with 29 bioxazoline (BiOx) and biimidazoline (BiIm) ligands revealed that enantioselectivity correlates with electronic properties of the ligands, with more electron-donating ligands affording higher ee's. Experimental and computational mechanistic studies were conducted, lending support to the hypothesis that reductive elimination is enantiodetermining and the electronic character of the ligands influences the enantioselectivity by altering the position of the transition state structure along the reaction coordinate. This study demonstrates the benefits of utilizing statistical modeling as a platform for mechanistic understanding and provides new insight into an emerging class of chiral ligands for stereoconvergent Ni and Ni/photoredox cross-coupling.
Visible-Light-Induced Charge Transfer Enables Csp3-H Functionalization of Glycine Derivatives: Access to 1,3-Oxazolidines
Li, Ying,Xie, Zhixiang,Yang, Xiaorong,Zhang, Yuan,Zhu, Yin
supporting information, p. 1638 - 1643 (2020/03/13)
A photoredox catalyst free, visible-light-induced aerobic oxidative [2 + 3] cycloaddition reaction between glycine derivatives and styrene oxides has been disclosed that provides an efficient approach for the rapid synthesis of 1,3-oxazolidines under mild
Use of allylzinc halide as a source of halide: Differential addition of nucleophiles to Ts-aziridines and aldehydes under similar reaction conditions
Chatterjee, Rana,Samanta, Satyajit,Mukherjee, Anindita,Santra, Sougata,Zyryanov, Grigory V.,Majee, Adinath
supporting information, p. 276 - 283 (2019/01/04)
We have observed that the allylic zinc halide under identical reaction conditions acts in different modes for different electrophiles. For Ts-aziridines the halide part of the allylic halide has been introduced as a nucleophile and for the carbonyl compou
Palladium-Catalyzed Intermolecular Heck-Type Reaction of Epoxides
Teng, Shenghan,Tessensohn, Malcolm E.,Webster, Richard D.,Zhou, Jianrong Steve
, p. 7439 - 7444 (2018/07/15)
The palladium-catalyzed intermolecular Heck-type reaction of both cyclic and acyclic epoxides is reported with tolerance of typical polar groups and acidic protons. Suitable alkenes include styrenes, conjugate dienes, and some electron-deficient olefins. In reactions of aliphatic terminal epoxides, ring opening occurs selectively at terminal positions, and stereocenters of epoxides are fully retained. Mechanistic studies provide evidence for in situ conversion of epoxides to β-halohydrins, generation of alkyl radicals, and radical addition to alkenes as key steps. Cyclovoltammetric determination of reduction potentials suggests that during activation of alkyl iodides by palladium(0) complexes, inner-sphere halogen abstraction is more likely than outer-sphere single electron transfer.
Intermolecular Tandem Addition/Esterification Reaction of Alkenes with Malonates Leading to γ-Lactones Mediated by Molecular Iodine under Visible Light Irradiation
Maejima, Saki,Yamaguchi, Eiji,Itoh, Akichika
supporting information, p. 3883 - 3887 (2017/09/18)
The iodine-mediated intermolecular C?C bond-forming/esterification reaction of various alkenes including α-olefins with malonates under irradiation using a compact fluorescent lamp has been developed to synthesize γ-lactones in moderate to excellent yield
1,3,2,4-diazadiphosphetidine-based phosphazane oligomers as source of P(III) atom economy reagents: Conversion of epoxides to vic -haloalcohols, vic -dihalides, and alkenes in the presence of halogen sources
Iranpoor, Nasser,Firouzabadi, Habib,Etemadidavan, Elham
, p. 1165 - 1173 (2014/10/16)
1,3,2,4-Diazadiphosphetidines (P1-P3), as easily prepared, stable, and heterogeneous P(III) compounds, were used for the efficient conversion of epoxides to vic-halohydrins, vic-dihalides, or alkenes in the presence of different halogen sources in CH3CN. Of these phosphazanes, P3 is most suitable and contains 4 phosphorous atoms with the advantage of having greater atom economy and its phosphorus oxide byproduct can be easily separated from the reaction mixture by simple filtration. The nitrogen atoms in this molecule can also act as acid scavengers in the reaction.
An improved protocol for regioselective ring-opening of sulfonyl aziridines with iodine promoted by PPh3
Zhang, Jinfeng,Meng, Lingguo,Li, Chuntao,Xiao, Guoyuan
, p. 1508 - 1512 (2014/01/06)
A new route to synthesize β-iodo amines from sulfonyl aziridines and iodine was developed in the presence of PPh3. This ring-opening reaction was an efficient and simple process to give β-iodo amines in excellent yields with high chemoselectivi
H2TPP organocatalysis in mild and highly regioselective ring opening of epoxides to halo alcohols by means of halogen elements
Torabi, Parviz,Azizian, Javad,Zomorodbakhsh, Shahab
scheme or table, p. 5508 - 5519 (2012/08/28)
We found that elemental iodine and bromine are converted to trihalide nucleophiles (triiodine and tribromide anion, respectively) in the presence of catalytic amounts of meso-tetraphenylporphyrins (H2TPP). Therefore a highly regioselective method for the synthesis of β-haloalcohols through direct ring opening of epoxides with elemental iodine and bromine in the presence of H2TPPs as new catalysts is described. At room temperature a series of epoxide derivatives were converted into the corresponding halohydrins resulting from an attack of trihalide species anion atoms at the less substituted carbon atom. This method occurs under neutral and mild conditions with high yields in various aprotic solvents, even when sensitive functional groups are present.
A one-pot regioselective synthetic route to vinyl sulfones from terminal epoxides in aqueous media
Chawla, Ruchi,Kapoor, Ritu,Singh, Atul K.,Yadav, Lal Dhar S.
experimental part, p. 1308 - 1313 (2012/06/01)
A highly efficient LiBr catalysed regioselective synthesis of vinyl sulfones from readily available terminal epoxides and sodium sulfinates in a one-pot procedure using water as a reaction medium is reported. The protocol is adorned with several attributes of green chemistry like recycling of the catalyst, atom-economy and an aqueous medium.
Direct reaction of aryl iodides with activated aluminium powder and reactions of the derived aryl sesquiiodides
Tang, Xiaoping,Rawson, Daniel,Woodward, Simon
scheme or table, p. 636 - 638 (2010/09/18)
High temperature (110-120 °C) direct reaction of ArI (Ar = Ph, 1-C 10H7, 3-Tol) with aluminium powder in the presence of HgCl2 (1 mol%) or liquid gallium metal (10mol%) leads to quantitative conversion to the aryl sesquiiodides Al2Ar3I3. The latter, highly Lewis acidic, compounds are effective in opening of cyclic ethers and direct ester to amide conversions. Georg Thieme Verlag Stuttgart.
