27356-88-3Relevant academic research and scientific papers
Redox-active alkylsulfones as precursors for alkyl radicals under photoredox catalysis
Patel, Sandeep,Paul, Biprajit,Paul, Hrishikesh,Shankhdhar, Rajat,Chatterjee, Indranil
, p. 4857 - 4860 (2022/04/19)
A method for generating alkyl radicals using visible-light photoredox catalysis is described. This procedure was found to present an efficient means to access a diverse collection of 1°, 2°, and 3° alkyl radicals through the single-electron transfer of sulfones under mild reaction conditions. These alkyl radicals generated via the reductive desulfonylation of readily synthesized and stable alkylsulfones were engaged to forge C-C bonds. A detailed study was also carried out to shed light on the mechanism.
A General Approach to Deboronative Radical Chain Reactions with Pinacol Alkylboronic Esters
André-Joyaux, Emy,Kuzovlev, Andrey,Renaud, Philippe,Tappin, Nicholas D. C.
, p. 13859 - 13864 (2020/06/10)
The generation of carbon-centered radicals from air-sensitive organoboron compounds through nucleohomolytic substitution at boron is a general method to generate non-functionalized and functionalized radicals. Due to their reduced Lewis acidity, alkylboronic pinacol esters are not suitable substrates. We report their in situ conversion into alkylboronic catechol esters by boron-transesterification with a substoichiometric amount of catechol methyl borate combined with an array of radical chain processes. This simple one-pot radical-chain deboronative method enables the conversion of pinacol boronic esters into iodides, bromides, chlorides, and thioethers. The process is also suitable the formation of nitriles and allylated compounds through C?C bond formation using sulfonyl radical traps. The power of combining radical and classical boron chemistry is illustrated with a modular 5-membered ring formation using a combination of three-component coupling and protodeboronative cyclization.
Alkylation of Allyl/Alkenyl Sulfones by Deoxygenation of Alkoxyl Radicals
Han, Jia-Bin,Guo, Ao,Tang, Xiang-Ying
supporting information, p. 2989 - 2994 (2019/02/05)
A challenging deoxygenation of alkoxyl radicals from readily accessible alcohol derivatives was developed, affording facile synthesis of functionalized alkenes with good functional group tolerance under mild reaction conditions. Because alkoxyl radicals can easily undergo β-fragmentations or hydrogen abstractions, this new strategy for deoxygenation of alkoxyl radicals is highly valuable. Moreover, mechanistic studies revealed that the electron-neutral phosphine acts as the deoxygenation reagent.
Switchable C-H Functionalization of N-Tosyl Acrylamides with Acryloylsilanes
Song, Shengjin,Lu, Ping,Liu, Huan,Cai, Sai-Hu,Feng, Chao,Loh, Teck-Peng
, p. 2869 - 2872 (2017/06/13)
A controllable Rh-catalyzed protocol to access alkylation and alkenylation-annulation of N-tosyl acrylamide with acryloyl silane is reported. In contrast to the directing group or catalyst-dependent divergent sp2 C-H alkylation/alkenylation, the intrinsic property of acryloylsilane allows the switchable reaction manifold, thereby affording either alkylation or annulation products with slight modification of the reaction conditions.
Stereoselective synthesis of Z-vinylsilanes via palladium-catalyzed direct intermolecular silylation of C(sp2)-H bonds
Pan, Jin-Long,Chen, Chao,Ma, Zhi-Gang,Zhou, Jia,Wang, Li-Ren,Zhang, Shu-Yu
supporting information, p. 5216 - 5219 (2017/11/06)
An efficient and convenient palladium-catalyzed direct intermolecular silylation of C(sp2)-H bonds by using disilanes as the silicon source with the assistance of a readily removable bidentate directing group is reported. This strategy provided a regio- and stereoselective protocol for exclusive synthesis of Z-vinylsilanes with reasonable to excellent yields and good functional group compatibility. Silylation of the isolated palladacycle intermediate revealed the Z-stereoselective pathway. Moreover, the practicality and effectiveness of this method were illustrated by a gram-scale experiment and further functionalization of the silylation product.
Stereo- and chemoselective cross-coupling between two electron-deficient acrylates: An efficient route to (Z, E)-muconate derivatives
Hu, Xu-Hong,Zhang, Jian,Yang, Xiao-Fei,Xu, Yun-He,Loh, Teck-Peng
supporting information, p. 3169 - 3172 (2015/03/30)
A Ru-catalyzed direct oxidative cross-coupling reaction of acrylates was developed. It offers a straightforward and atom-economical protocol for the synthesis of functionalized (Z,E)-muconate derivatives in moderate to good yields with good stereo- and chemoselectivities. The conjugated muconates bearing differentiable terminal functionality can be selectively transformed into versatile synthetic intermediates widely used in organic synthesis.
Rhodium(III)-catalyzed olefinic C-H alkynylation of acrylamides using tosyl-imide as directing group
Feng, Chao,Feng, Daming,Luo, Yang,Loh, Teck-Peng
supporting information, p. 5956 - 5959 (2015/01/08)
The Rh(III)-catalyzed C-H alkynylation of acrylamide derivative is realized using a hypervalent alkynyl iodine reagent. The use of a weakly coordinating directing group proved to be of critical importance. This reaction displays broad functional group tolerance and high efficiency, which opens a new synthetic pathway to access functionalized 1,3-enyne skeletons.
Preparation of alkylmagnesium reagents from alkenes through hydroboration and boron-magnesium exchange
Reichle, Markus A.,Breit, Bernhard
, p. 5730 - 5734 (2012/08/14)
Tolerant: Alkylmagnesium reagents can be synthesized from alkenes through a sequence of hydroboration and subsequent boron-magnesium exchange using a method that tolerates different functional groups (see scheme). The resulting alkylmagnesium reagents can be used in carbon-carbon bond forming reactions, such as alkylation reactions or transition-metal-catalyzed cross-coupling reactions. Copyright
Phosphinic pseudo-tripeptides as potent inhibitors of matrix metalloproteinases: A structure-activity study
Vassiliou, Stamatia,Mucha, Artur,Cuniasse, Philippe,Georgiadis, Dimitris,Lucet-Levannier, Karine,Beau, Fabrice,Kannan, Rama,Murphy, Gillian,Kn?uper, Vera,Rio, Marie-Christine,Basset, Paul,Yiotakis, Athanasios,Dive, Vincent
, p. 2610 - 2620 (2007/10/03)
Several phosphinic pseudo-tripeptides of general formula R-XaaΨ(PO2- CH2)Xaa'-Yaa'-NH2 were synthesized and evaluated for their in vitro activities to inhibit stromelysin-3, gelatinases A and B, membrane type-1 matrix metalloproteinase, collagenases 1 and 2, and matrilysin. With the exception of collagenase-1 and matrilysin, phosphinic pseudo-tripeptides behave as highly potent inhibitors of matrix metalloproteinases, provided they contain in P1' position an unusual long aryl-alkyl substituent. Study of structure-activity relationships regarding the influence of the R and Xaa' substituents in this series may contribute to the design of inhibitors able to block only a few members of the matrix metalloproteinase family.
Substituted oxiranecarboxylic acids, their use and medicaments containing them
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, (2008/06/13)
Substituted oxiranecarboxylic acids of the formula STR1 wherein R1 denotes a hydrogen atom (--H), a halogen atom, a hydroxylroup, a lower alkyl group, a lower alkoxy group or a trifluoromethyl group, R2 has one of the meanings of Rs
