54766-51-7Relevant articles and documents
An efficient iodine pentoxide-triggered iodocarbocyclization for the synthesis of iodooxindoles in water
Zhang, Ming-Zhong,Wang, Xin,Gong, Ming-Ying,Chen, Lin,Shi, Wen-Bing,He, Shu-Hua,Jiang, Yong,Chen, Tieqiao
supporting information, p. 5197 - 5202 (2018/07/29)
An efficient iodocarbocyclization of alkenes for the synthesis of iodooxindoles has been developed. This reaction proceeds in a chemoselective manner and shows excellent tolerance of various functional groups, including a chemosensitive hydroxymethyl grou
Iodide reagent controlled reaction pathway of iodoperoxidation of alkenes: A high regioselectivity synthesis of α- And β-iodoperoxidates under solvent-free conditions
Gao, Xiaofang,Yang, Hongling,Cheng, Chen,Jia, Qi,Gao, Fang,Chen, Hongxiang,Cai, Qun,Wang, Chuangjian
, p. 2225 - 2230 (2018/05/30)
A highly atom economical, efficient and environmentally friendly iodoperoxidation of alkenes with tert-butyl hydroperoxide (TBHP) and iodide/iodine is reported in this paper. This method afforded a convenient path to obtain two different configurations of iodoperoxidates from the same starting materials. Notably, the regiodivergent iodoperoxidation reaction was achieved by using different iodide reagents. A series of control experiments were performed, which suggested the involvement of a radical pathway for the anti-Markovnikov type iodoperoxidates (α) in the combination of ammonium iodide (NH4I)/TBHP, and an active cationic iodine pathway for the Markovnikov type adduct (β) with iodine (I2) and TBHP.
Regioselective vicinal functionalization of unactivated alkenes with sulfonium iodate(i) reagents under metal-free conditions
Rao, Dodla S.,Reddy, Thurpu R.,Babachary, Kalvacherla,Kashyap, Sudhir
, p. 7529 - 7543 (2016/08/16)
Metal-free, molecular iodine-free direct 1,2-difunctionalization of unactivated alkenes has been reported. The sulfonium iodate(i) reagent efficiently promoted the intermolecular vicinal iodo-functionalization of a diverse range of olefins in a stereo and regioselective manner. This method enables the divergent and straightforward preparation of synthetically useful functionalities; β-iodocarboxylates, β-iodohydrins, and β-iodoethers in a one-step process. Further interconversion of iodo-functionalized derivatives allows easy access to valuable synthetic intermediates en route to biologically active molecules.
Combination of NH2OH·HCl and NaIO4: an effective reagent for molecular iodine-free regioselective 1,2-difunctionalization of olefins and easy access of terminal acetals
Chakraborty, Nirnita,Santra, Sougata,Kundu, Shrishnu Kumar,Hajra, Alakananda,Zyryanov, Grigory V.,Majee, Adinath
, p. 56780 - 56788 (2015/07/15)
We have demonstrated a new application of our oxidizing reagent, a combination of NH2OH·HCl and NaIO4, in the first generalized regioselective 1,2-difunctionalization of olefins. It is a general method for the preparation of β-iodo-β′-hydroxy ethers, β-iodo ethers, β-iodohydrin, and β-iodo acetoxy compounds using different reaction media. The reactions are highly regioselective, always affording Markovnikov's type addition products. The methodology is also applicable for the easy access of terminal acetals. Molecular iodine-free synthesis, room temperature reaction conditions, high yields, use of less expensive reagents, mild reaction conditions, broad applicability of nucleophiles, and applicability for gram-scale synthesis are the notable advantages of this present protocol.
m-Iodosylbenzoic acid, a tagged hypervalent iodine reagent for the iodo-functionalization of alkenes and alkynes
Yusubov, Mekhman S.,Yusubova, Roza Ya.,Kirschning, Andreas,Park, Joo Yeon,Chi, Ki-Whan
, p. 1506 - 1509 (2008/09/19)
An efficient and facile method for the iodo-functionalization of alkenes 5 and alkynes 6 by using recyclable m-iodosylbenzoic acid (2) was developed. The final products can be easily isolated without any chromatographic purification by simple treatment of the crude mixture with an anionic exchange resin. Unreacted m-iodosylbenzoic acid and reduced m-iodobenzoic acid are effectively recovered from the resin by acidification with hydrochloric acid.
(Dichloroiodo)benzene - An Easily Available Reagent for Chloro- and Iodoalkoxylation, Iodohydroxylation, and Iodochlorination of Alkenes
Yusubov,Yusubova,Filimonov,Chi, Ki-Whan
, p. 443 - 450 (2007/10/03)
A convenient synthesis of vicinal methoxychlorides, methoxyiodides, iodhydrines and iodochloride from alkenes using PhICl2/CH 3OH, I2/ PhICl2/CH3OH, I 2/PhICl2/CH3CN/H2O and I 2/PhICl2/CH2Cl2 is described.
Reaction of Alkenes with Hydrogen Peroxide and Sodium Iodide: A Nonenzymatic Biogenic-Like Approach to Iodohydrins
Barluenga, Jose,Marco-Arias, Maria,Gonzalez-Bobes, Francisco,Ballesteros, Alfredo,Gonzalez, Jose M.
, p. 1677 - 1682 (2007/10/03)
An efficient protocol to synthesize iodohydrins from alkenes is presented. Reactions were conducted in aqueous media using safe and readily available sodium iodide (the most abundant form of the element), and a highly convenient oxidant such as hydrogen peroxide. Addition of a protic acid triggers a faster and efficient process, a role formally related to that played by haloperoxidase enzymes in naturally occurring transformations. The successful application of these conditions to multigram scale preparations and over natural products derivatives is also discussed.
Solid-state organic reactions proceeding by pulverization: Oxidation and halogenation with iodosobenzene and inorganic solid-supports
Sohmiya, Hajime,Kimura, Takahide,Fujita, Mitsue,Ando, Takashi
, p. 13737 - 13750 (2007/10/03)
Pulverization-activation method was employed to accelerate solid-state organic reactions. Crushing and grinding of solid mixtures of hydrogen halide-treated silica gels, iodosobenzene and organic substrates in the absence of a solvent brought about smooth and rapid reactions to give halogenated and/or oxidized products in good yields. Various sulfides were smoothly converted to sulfonyl chlorides in one step in excellent yields. The surface of silica gel activated by pulverization serves as a reaction field on which reagent molecules can effectively encounter with each other.
