125763-63-5Relevant academic research and scientific papers
Two-Step Protocol for Iodotrimethylsilane-Mediated Deoxy-Functionalization of Alcohols
Chen, Yuming,He, Ru,Song, Hongjian,Yu, Guoqing,Li, Chenglin,Liu, Yuxiu,Wang, Qingmin
supporting information, p. 1179 - 1183 (2021/02/01)
We have developed a two-step protocol for iodotrimethylsilane-mediated deoxy-functionalization of primary and secondary alcohols to afford products containing a C?N, C?S, or C?O bond. In the first step the alcohol undergoes iodination with iodotrimethylsilane, and in the second, the iodine atom is replaced by a N, S, or O nucleophile. Compared with traditional Mitsunobu reaction, non-acidic pre-nucleophiles can be used, and the reaction proceeds with retention of configuration. This operationally simple, highly efficient protocol can be used for some natural products and small-molecule drugs containing hydroxy-group.
Ready access to organoiodides: Practical hydroiodination and double-iodination of carbon-carbon unsaturated bonds with I2
Xiao, Jing,Han, Li-Biao
, p. 3510 - 3515 (2019/05/17)
By using I2 or I2/H3PO3 system, various alkenes and alkynes were converted to the corresponding alkyl and alkenyl iodides in good yields. In the presence of I2, alkynes could be di-iodinated using H2O as the solvent in air at room temperature. This method also features the simple work-up procedure since the pure product could be obtained by extraction. Additionally, for the first time, combining with the non-toxic and cheap phosphonic acid H3PO3, alkenes and alkynes were also hydroiodinated successfully, which provides a simple and practical approach for synthesis of organoiodides.
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.
An expedient stereoselective synthesis of (Z)- and (E)-allyl iodides from Baylis-Hillman adducts along with selective iodination of benzylic alcohols using the polymethylhydrosiloxane-iodine system
Das, Biswanath,Holla, Harish,Srinivas, Yallamalla,Chowdhury, Nikhil,Bandgar
, p. 3201 - 3204 (2007/10/03)
A stereoselective method has been developed for the synthesis of (Z)- and (E)-allyl iodides from Baylis-Hillman adducts using polymethylhydrosiloxane (PMHS) and iodine in chloroform at room temperature. In addition, the reagent system has been utilized for the iodination of benzylic alcohols selectively.
An efficient and facile hydroiodination of alkenes and alkynes PI using polymethylhydrosiloxane-iodine system
Das, Biswanath,Srinivas, Yallamalla,Holla, Harish,Narender, Ravirala
, p. 800 - 801 (2008/02/09)
A mild and efficient method has been developed for the synthesis of alkyl and alkenyl iodides from alkenes and alkynes using polymethylhydrosiloxane (PMHS) and iodine in chloroform at room temperature. The reagent system generates hydrogen iodide which regioselectively adds to the alkenes and alkynes. Copyright
Diiodosilane. 2. A Multipurpose Reagent for Hydrolysis and Reductive Iodination of Ketals, Acetals, Ketones, and Aldehydes
Keinan, E.,Perez, D.,Sahai, M.,Shvily, R.
, p. 2927 - 2938 (2007/10/02)
The reaction patterns of diiodosilane (SiH2I2, DIS) with ketals, acetals, ketones, and aldehydes were explored.The reagent may be used for mild cleavage of ketals and acetals either hydrolytically to give the parent carbonyl functionality or reductively to produce the corresponding alkyl iodide.At low temperatures (-42 deg C) and short reaction times (few minutes), catalytic amounts (5-10 molpercent) of DIS provide clean deprotection of various ketals and acetals to yield ketones and aldehydes, with no apparent reduction of the latter.At temperatures above 0 deg C, DIS effectively reduces ketals and acetals to iodoalkanes.This reduction is quite general both with respect to ketals and acetals and unprotected ketones and aldehydes.Reaction rates, however, are strikingly dependent on the substrate, with the following tendencies: (a) aromatic functionalities are generally reduced much faster than their aliphatic analogues; (b) ketals and acetals are rapidly reduced to the corresponding iodoalkanes, while free aldehydes, and particularly ketones, are essentially inert under the reaction conditions (but can be significantly activated by catalytic amounts of iodine); (c) dimethyl ketals form the parent ketones preferentially, while all other ketals, including diethyl ketals and dioxolanes, are reduced to iodoalkanes.
