1846-20-4Relevant academic research and scientific papers
Triethylaluminum- or triethylborane-induced free radical reaction of alkyl iodides and α,β-unsaturated compounds
Liu, Jing-Yuan,Jang, Yoeng-Jiunn,Lin, Wen-Wei,Liu, Ju-Tsung,Yao, Ching-Fa
, p. 4030 - 4038 (2003)
A series of α,β-unsaturated compounds, 1a-c, 9, 13, and 17, were used as reactants in free radical conjugate addition reactions with different radicals generated from alkyl iodides such as 3, 4, or 5 in the presence of triethylborane-oxygen in air or via the use of triethylaluminum-benzoyl peroxide as a free radical initiator. When the reactions were carried out using triethylborane-air, the products, in most cases, were clean and were easily purified. However, higher yields of the 1,4-adducts and less side reactions occurred when less reactive substrates were used as Michael acceptors in reactions with triethylaluminum-benzoyl peroxide and alkyl iodide under similar conditions. A mechanism for this is proposed in Scheme 1.
Iron-Catalyzed Photoredox Functionalization of Methane and Heavier Gaseous Alkanes: Scope, Kinetics, and Computational Studies
Zhang, Qingqing,Liu, Shuyang,Lei, Jinglan,Zhang, Yongqiang,Meng, Changgong,Duan, Chunying,Jin, Yunhe
, p. 1901 - 1906 (2022/03/27)
Herein, we report the development of the photocatalytic C-H functionalization of methane, ethane, and heavier gaseous alkanes with good yields and selectivity, broad scope (57 examples), mild conditions, and low cost. Kinetics and density functional theor
Convenient C(sp3)-H bond functionalisation of light alkanes and other compounds by iron photocatalysis
Duan, Chunying,Jin, Yunhe,Meng, Changgong,Wang, Lifang,Wang, Xinyao,Zhang, Qingqing
supporting information, p. 6984 - 6989 (2021/09/28)
Light alkanes are natural organic carbon sources and widely distributed in nature. Transforming them into value-added fine chemicals affords attractively economic and ecological benefits as well as enormous chemical challenges. Herein, we report a practical iron-catalysed photoredox system for C(sp3)-H transformation of ethane, propane, and other light alkanes to C-N and C-C bonds under ambient temperature. The present method with abundant and inexpensive iron salts as photocatalysts exhibits high catalytic efficiency (turnover number up to 8000), mild conditions, and the convenience of being purified and scaled up without chromatography. A photo-induced ligand-to-metal charge transfer between Fe(iii) and Cl- generates a highly active chlorine radical that sequentially acts as hydrogen atom transfer catalyst. Therefore, the sustainable, convenient, and environmentally friendly system will find wide applications in high-value-added transformation of natural alkanes with novel inspiration not only for organic synthesis, but also for designing catalytically active organic/inorganic materials. This journal is
Radical hydroalkylation and hydroacylation of alkenes by the use of benzothiazoline under thermal conditions
Akiyama, Takahiko,Uchikura, Tatsuhiro,Toda, Mitsuhiro,Mouri, Toshiki,Fujii, Tatsuya,Moriyama, Kaworuko,Ibanez, Ignacio
, p. 12715 - 12723 (2020/11/09)
The hydroalkylation and hydroacylation of electrondeficient alkenes proceeded smoothly by using benzothiazoline derivatives as radical-transfer reagents under thermal conditions without light irradiation or any additive. Both benzyl and benzoyl moieties were transferred efficiently.
C(sp3)-H functionalizations of light hydrocarbons using decatungstate photocatalysis in flow
Deng, Yuchao,Fagnoni, Maurizio,Guthrie, Duncan,Laudadio, Gabriele,No?l, Timothy,Nun?, Manuel,Ravelli, Davide,Sun, Yuhan,Wal, Klaas Van Der
, p. 92 - 96 (2020/09/03)
Direct activation of gaseous hydrocarbons remains a major challenge for the chemistry community. Because of the intrinsic inertness of these compounds, harsh reaction conditions are typically required to enable C(sp3)-H bond cleavage, barring potential applications in synthetic organic chemistry. Here, we report a general and mild strategy to activate C(sp3)-H bonds in methane, ethane, propane, and isobutane through hydrogen atom transfer using inexpensive decatungstate as photocatalyst at room temperature. The corresponding carbon-centered radicals can be effectively trapped by a variety of Michael acceptors, leading to the corresponding hydroalkylated adducts in good isolated yields and high selectivity (38 examples).
One-pot synthesis of malononitriles by free radical reactions of ylidenemalononitrile with Et3B and iodoalkane in a water-ether biphase medium
Tu, Zhijay,Lin, Chunchi,Jang, Yaochung,Jang, Yeong-Jiunn,Ko, Shengkai,Fang, Hulin,Liu, Ju-Tsung,Yao, Ching-Fa
, p. 6133 - 6137 (2007/10/03)
The one-pot synthesis of malononitrile derivatives 4, 6, and 7 in moderate to high yields by the reaction of ylidenemalononitriles 3, prepared in situ from carbonyl compounds 1 and malononitrile 2 in the presence of ammonium acetate in aqueous solution at
A Novel Photoalkylation of Electron-deficient Alkenes by Use of Organotin Compounds via Photoinduced Electron Transfer
Mizuno, Kazuhiko,Nakanishi, Kazuhisa,Tachibana, Atsushi,Otsuji, Yoshio
, p. 344 - 345 (2007/10/02)
Irradiation of 1-aryl-2,2-dicyanoethenes and tetraalkylstannanes in propionitrile in the presence of phenanthrene afforded regioselectively 1-alkyl-1-aryl-2,2-dicyanoethanes in good yields.
