29527-87-5Relevant articles and documents
Merging Halogen-Atom Transfer (XAT) and Copper Catalysis for the Modular Suzuki-Miyaura-Type Cross-Coupling of Alkyl Iodides and Organoborons
Górski, Bartosz,Leonori, Daniele,Zhang, Zhenhua
supporting information, (2022/02/01)
We report here a mechanistically distinct approach to achieve Suzuki-Miyaura-type cross-couplings between alkyl iodides and aryl organoborons. This process requires a copper catalyst but, in contrast with previous approaches based on palladium and nickel
Visible-light-mediated multicomponent reaction for secondary amine synthesis
Wang, Xiaochen,Zhu, Binbing,Dong, Jianyang,Tian, Hao,Liu, Yuxiu,Song, Hongjian,Wang, Qingmin
supporting information, p. 5028 - 5031 (2021/05/28)
The widespread presence of secondary amines in agrochemicals, pharmaceuticals, natural products, and small-molecule biological probes has inspired efforts to streamline the synthesis of molecules with this functional group. Herein, we report an operationally simple, mild protocol for the synthesis of secondary amines by three-component alkylation reactions of imines (generated in situ by condensation of benzaldehydes and anilines) with unactivated alkyl iodides catalyzed by inexpensive and readily available Mn2(CO)10. This protocol, which is compatible with a wide array of sensitive functional groups and does not require a large excess of the alkylating reagent, is a versatile, flexible tool for the synthesis of secondary amines.
Photochemical Decarboxylative C(sp3)-X Coupling Facilitated by Weak Interaction of N-Heterocyclic Carbene
Chen, Kun-Quan,Wang, Zhi-Xiang,Chen, Xiang-Yu
, p. 8059 - 8064 (2020/11/02)
While N-hydroxyphthalimide (NHPI) ester has emerged as a powerful reagent as an alkyl radical source for a variety of C-C bond formations, the corresponding C(sp3)-N bond formation is still in its infancy. We demonstrate herein transition-metal-free decarboxylative C(sp3)-X bond formation enabled by the photochemical activity of the NHPI ester-NaI-NHC complex, giving primary C(sp3)-(N)phth, secondary C(sp3)-I, or tertiary C(sp3)-(meta C)phth coupling products. The primary C(sp3)-(N)phth coupling offers convenient access to primary amines.
Synthesis of Nitrile-Bearing Quaternary Centers by an Equilibrium-Driven Transnitrilation and Anion-Relay Strategy
Alazet, Sébastien,West, Michael S.,Patel, Purvish,Rousseaux, Sophie A. L.
supporting information, p. 10300 - 10304 (2019/07/04)
The efficient preparation of nitrile-containing building blocks is of interest due to their utility as synthetic intermediates and their prevalence in pharmaceuticals. As a result, significant efforts have been made to develop methods to access these motifs which rely on safer and non-toxic sources of CN. Herein, we report that 2-methyl-2-phenylpropanenitrile is an efficient, non-toxic, electrophilic CN source for the synthesis of nitrile-bearing quaternary centers by a thermodynamic transnitrilation and anion-relay strategy. This one-pot process leads to nitrile products resulting from the gem-difunctionalization of alkyl lithium reagents.
Method of preparing iodine alkane by using rhodium catalysis
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Paragraph 0044-0045, (2018/04/03)
The invention relates to the field of organic synthesis and discloses a synthetic method of iodine alkane. The synthetic method of the iodine alkane, disclosed by the invention, comprises the following steps: taking olefin as a starting raw material, adding a rhodium metal catalyst, a phosphine ligand, a solvent and molecular iodine into a pressurizing reaction kettle, introducing hydrogen and then synthesizing a series of the iodine alkane by using one-step reaction. The reaction temperature is 0 to 60 DEG C, the molar ratio of the rhodium metal to the olefin is (0.00001 to 1) to (0.1 to 1) and the molar ratio of the iodine to the olefin is (0.5 to 1) to (10 to 1). The synthetic method of the iodine alkane, disclosed by the invention, has obvious advantages of wide application range, short process flow and low cost of the raw materials; the synthetic method of the iodine alkane is suitable for industrialized production of a series of the iodine alkanes.
Rhodium-Catalyzed Generation of Anhydrous Hydrogen Iodide: An Effective Method for the Preparation of Iodoalkanes
Zeng, Chaoyuan,Shen, Guoli,Yang, Fan,Chen, Jingchao,Zhang, Xuexin,Gu, Cuiping,Zhou, Yongyun,Fan, Baomin
supporting information, p. 6859 - 6862 (2018/10/25)
The preparation of anhydrous hydrogen iodide directly from molecular hydrogen and iodine using a rhodium catalyst is reported for the first time. The anhydrous hydrogen iodide generated was proven to be highly active in the transformations of alkenes, phenyl aldehydes, alcohols, and cyclic ethers to the corresponding iodoalkanes. Therefore, the present methodology not only has provided convenient access to anhydrous hydrogen iodide but also offers a practical preparation method for various iodoalkanes in excellent atom economy.
Method for the Preparation of Iodoalkanes
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Paragraph 0036, (2017/08/07)
The present invention relates to an atom economic procedure of preparing iodoalkanes by hydroiodination of alkenes. In particular the present method features the generation of anhydrous hydrogen iodide from atomic hydrogen and iodine in situ by using transition metal precursor and phosphine ligandcatalyst.
Mild and phosphine-free iron-catalyzed cross-coupling of nonactivated secondary alkyl halides with alkynyl grignard reagents
Cheung, Chi Wai,Ren, Peng,Hu, Xile
supporting information, p. 2566 - 2569 (2014/05/20)
A simple protocol for iron-catalyzed cross-coupling of nonactivated secondary alkyl bromides and iodides with alkynyl Grignard reagents at room temperature has been developed. A wide range of secondary alkyl halides and terminal alkynes are tolerated to a
A real time reaction monitoring using fluorescent dansyl group as a solid-phase leaving group
Suenaga, Toshiro,Schutz, Caroline,Nakata, Tadashi
, p. 5799 - 5801 (2007/10/03)
A real time monitoring method to monitor the progress of the solid-phase reaction has been developed. The substitution reaction on the solid-phase was clearly monitored as a change in the color depth using the fluorescent dansyl group as the leaving group. This methodology is applicable to both parallel and split combinatorial synthesis.
Nucleophilic substitution of 1-phenyl-2-phenyl telluropropane to yield 2-halo-1-phenylpropanes
Ogura, Fumio,Okada, Yoshiharu,Nishimura, Naoko,Hamamoto, Kenichiro,Miyakawa, Makoto,Otsubo, Tetsuo,Aso, Yoshio,Inoue, Shinobu,Tsutsui, Koji
, p. 203 - 210 (2007/10/03)
Mechanism of a novel transformation of the alkyl phenyltellurides to alkyl halides via nucleophilic substitution of the phenyltelluro group in organotelluriums is studied on the basis of kinetics and stereochemistry using the titled chiral substrate. The results obtained strongly suggest that the substitutions proceed via SN2 mechanism with Walden inversion and very low Arrhenius' energies of activation.