7387-75-9Relevant articles and documents
Silica gel-mediated hydrohalogenation of unactivated alkenes using hydrohalogenic acids under organic solvent-free conditions
Tanemura, Kiyoshi
supporting information, p. 4293 - 4298 (2018/11/10)
Silica gel-mediated hydrochlorination of unactivated alkenes using 35% hydrochloric acid under organic solvent-free conditions proceeded to give the corresponding chlorides in good yields. Hydrobromination or hydriodination using 47% hydrobromic acid or 55% hydriodic acid afforded the corresponding halides, respectively. Silica gel could be recycled five times without any significant loss of activities.
Metal-free regioselective hydrochlorination of unactivated alkenes via a combined acid catalytic system
Liang, Shengzong,Hammond, Gerald B.,Xu, Bo
supporting information, p. 680 - 684 (2018/02/14)
A combined acid HCl/DMPU-acetic acid catalytic system was used in the hydrochlorination of a wide range of unactivated alkenes. This hydrochlorination strategy is remarkably greener than previous reported methods in terms of high atom efficiency, no toxic waste generated and metal-free process. The higher efficiency, compared with other commercially available HCl reagents, was augmented by the good regioselectivity and functionality tolerance found. A stepwise mechanism for this hydrochlorination process was proposed based on kinetic studies.
The direct anti-Markovnikov addition of mineral acids to styrenes
Wilger, Dale J.,Grandjean, Jean-Marc M.,Lammert, Taylor R.,Nicewicz, David A.
, p. 720 - 726 (2014/08/05)
The direct anti-Markovnikov addition of strong Bronsted acids to alkenes remains an unsolved problem in synthetic chemistry. Here, we report an efficient organic photoredox catalyst system for the addition of HCl, HF and also phosphoric and sulfonic acids to alkenes, with complete regioselectivity. These transformations were developed using a photoredox catalyst in conjunction with a redox-active hydrogen atom donor. The nucleophile counterion plays a critical role by ensuring high reactivity, with 2,6-lutidinium salts typically furnishing the best results. The nature of the redox-active hydrogen atom donor is also consequential, with 4-methoxythiophenol providing the best reactivity when 2,6-lutidinium salts are used. A novel acridinium sensitizer provides enhanced reactivity within several of the more challenging reaction manifolds. This Article demonstrates how nucleophilic addition reactions mediated by photoredox catalysis can change the way electrophilic and homofugal precursors are constructed.
