29478-23-7Relevant academic research and scientific papers
Reaction of trihaloisocyanuric acids with alkynes: An efficient methodology for the preparation of β-haloenol acetates
Crespo, Livia T.C.,Nogueira, Geisa P.,De Mattos, Marcio C.S.,Esteves, Pierre M.
, p. 205 - 214 (2018/02/07)
The reaction between trihaloisocyanuric acids and alkynes in the presence of acetic acid provides an efficient methodology for preparation of β-haloenol acetates in yields ranging from 34 to 94%, depending on the halogen and alkynes used. This methodology provides an alternative to typical procedures, which usually employ metal catalysis and are limited to terminal alkynes.
New synthetic approaches towards analogues of bedaquiline
Priebbenow, Daniel L.,Barbaro, Lisa,Baell, Jonathan B.
, p. 9622 - 9628 (2016/10/25)
Multi-drug resistant tuberculosis (MDR-TB) is of growing global concern and threatens to undermine increasing efforts to control the worldwide spread of tuberculosis (TB). Bedaquiline has recently emerged as a new drug developed to specifically treat MDR-
Regio- and stereoselective iodoacyloxylations of alkynes
Priebbenow, Daniel L.,Gable, Robert. W.,Baell, Jonathan
, p. 4412 - 4418 (2015/05/13)
A new method for the regioselective and stereoselective iodoacyloxylation of alkynes has been developed. This protocol utilizes a combination of an iodobenzene dicarboxylate and iodine to functionalize a series of activated and unactivated alkynes in an entirely selective and predictable fashion. The resultant iodo-enol esters were subsequently coupled with boronic acids to afford tetrasubstituted alkene derivatives, which could be further converted to the corresponding 1,1-disubstituted acetophenone.
Selective oxygenation of alkynes: A direct approach to diketones and vinyl acetate
Xia, Xiao-Feng,Gu, Zhen,Liu, Wentao,Wang, Ningning,Wang, Haijun,Xia, Yongmei,Gao, Haiyan,Liu, Xiang
supporting information, p. 9909 - 9913 (2015/01/09)
Arylalkynes can be converted into α-diketones with the use of a copper catalyst, and also be transformed into vinyl acetates under metal-free conditions, both in the presence of PhI(OAc)2 as an oxidant at room temperature. A series of substituted α-diketones were prepared in moderate to good yields. A variety of vinyl halides could be regio- and stereo-selectively synthesized under mild conditions, and I, Br and Cl could be all easily embedded into the alkynes. This journal is
Reactions of alkynes with iodine and potassium iodide in acetic acid in the presence of nitrates. Simple synthesis of 1-iodo-2-nitroalkenes
Yusubov,Perederina,Kulmanakova,Filimonov,Chi, Ki-Whan
, p. 1264 - 1272 (2007/10/03)
Terminal and internal alkynes react with I2 or KI and nitrates in acetic acid under mild conditions to give the corresponding 1-iodo-2-nitroalkenes as the major products. The effect of the reactant nature and reaction conditions on the yield of products was studied. Oxygen was found to play an important role in the formation of the target products. A possible mechanism of the reaction includes a series of redox transformations of I2 or I- and NO-3 to form INO2 which then adds to alkynes by a radical path. In reactions with potassium iodide, oxygen acts as an additional oxidant which converts NO into active nitrogen dioxide.
Stereoselective Bifunctionalization of Alkynes by Means of the Mercury(II) Salt-Iodine Combination
Barluenga, Jose,Martinez-Gallo, Jose M.,Najera, Carmen,Yus, Miguel
, p. 1017 - 1020 (2007/10/02)
The reaction of alkynes with iodine and mercury(II) salts (chloride, acetate, methanesulphonate, toluene-p-sulphonate, benzylsulphide, toluene-p-sulphinate, and thiocyanate) affords stereoselectively E-β-functionalized vinyl iodides resulting from the ionic addition of iodine and the mercury(II) salt anion.Unsymmetrical alkynes yield regiospecifically Markovnikov addition products.In the case of mercury(II) thiocyanate the reaction can be used also for the stereoselective preparation of E-1,2-dithiocyanatoalkenes.An ionic mechanism is proposed according to the observed regio- and stereochemistry.
