124920-12-3Relevant articles and documents
Heptadecafluorooctanesulfonic acid (C8F17SO3H) catalyzed intramolecular hydroamination of olefinic sulfonamides in fluorous biphase system (FBS)
Yin, Yan,Zhao, Gang
, p. 40 - 45 (2007)
A practical, efficient, and environmentally benign intramolecular hydroamination of olefinic sulfonamides was carried out in fluorous biphase system (FBS) using commercially available heptadecafluorooctanesulfonic acid (C8F17SO3
δ and α SP3 C-H bond oxidation of sulfonamides with PhI(OAc)2/I2 under metal-free conditions
Fan, Renhua,Pu, Dongming,Wen, Fengqi,Wu, Jie
, p. 8994 - 8997 (2007)
(Chemical Equation Presented) An efficient δ and α sp 3 C-H bond oxidation of sulfonamides with PhI(OAc)2/I 2 under metal-free conditions has been reported. The reaction provides a useful route to pyrrolidines, N-sulfonyli
Bis(trifluoromethanesulfonimide) (BSI): Acidity and application to hydrofunctionalization as a Br?nsted acid catalyst
Takagi, Ryukichi,Sakai, Yuichiro,Duong, Duyen Thi
, (2021/03/23)
A binaphthyl derivative, bearing bis(trifluoromethanesulfonimide) (BSI) moiety, was developed as a novel Br?nsted acid. Computational prediction of the pKa value of BSI indicated its classification as a strong Br?nsted acid. BSI catalyzed the h
Manganese-Catalyzed N-F Bond Activation for Hydroamination and Carboamination of Alkenes
Ji, Yun-Xing,Li, Jinxia,Li, Chun-Min,Qu, Shuanglin,Zhang, Bo
supporting information, p. 207 - 212 (2021/01/09)
A visible-light-promoted method for generating amidyl radicals from N-fluorosulfonamides via a manganese-catalyzed N-F bond activation strategy is reported. This protocol employs a simple manganese complex, Mn2(CO)10, as the precatalyst and a cheap silane, (MeO)3SiH, as both the hydrogen-atom donor and the F-atom acceptor, enabling intramolecular/intermolecular hydroaminations of alkenes, two-component carboamination of alkenes, and even three-component carboamination of alkenes. A wide range of valuable aliphatic sulfonamides can be readily prepared using these practical reactions.
Titanium-Catalyzed Hydroaminoalkylation of Ethylene
Rosien, Michael,T?ben, Iris,Schmidtmann, Marc,Beckhaus, Rüdiger,Doye, Sven
supporting information, p. 2138 - 2142 (2020/02/05)
The first examples of titanium-catalyzed hydroaminoalkylation reactions of ethylene with secondary amines are presented. The reactions can be achieved with various titanium catalysts and they do not require the use of high pressure equipment. In addition, the first solid-state structure of a titanapyrrolidine that is formed by insertion of an alkene into the Ti?C bond of a titanaaziridine is reported.
A Rh(III)-Catalyzed Formal [4+1] Approach to Pyrrolidines from Unactivated Terminal Alkenes and Nitrene Sources
Lee, Sumin,Lei, Honghui,Rovis, Tomislav
, p. 12536 - 12540 (2019/08/26)
We have developed a formal [4+1] approach to pyrrolidines from readily available unactivated terminal alkenes as 4-carbon partners. The reaction provides a rapid construction of various pyrrolidine containing structures, especially for the diastereoselect
Stereoinversion of Unactivated Alcohols by Tethered Sulfonamides
Marcyk, Paul T.,Jefferies, Latisha R.,AbuSalim, Deyaa I.,Pink, Maren,Baik, Mu-Hyun,Cook, Silas P.
supporting information, p. 1727 - 1731 (2019/01/21)
The direct, catalytic substitution of unactivated alcohols remains an undeveloped area of organic synthesis. Moreover, catalytic activation of this difficult electrophile with predictable stereo-outcomes presents an even more formidable challenge. Described herein is a simple iron-based catalyst system which provides the mild, direct conversion of secondary and tertiary alcohols to sulfonamides. Starting from enantioenriched alcohols, the intramolecular variant proceeds with stereoinversion to produce enantioenriched 2- and 2,2-subsituted pyrrolidines and indolines, without prior derivatization of the alcohol or solvolytic conditions.
Anodic benzylic C(sp3)-H amination: Unified access to pyrrolidines and piperidines
Herold, Sebastian,Bafaluy, Daniel,Mu?iz, Kilian
, p. 3191 - 3196 (2018/07/29)
An electrochemical aliphatic C-H amination strategy was developed to access the important heterocyclic motifs of pyrrolidines and piperidines within a uniform reaction protocol. The mechanism of this unprecedented C-H amination strategy involves anodic C-H activation to generate a benzylic cation, which is efficiently trapped by a nitrogen nucleophile. The applicability of the process is demonstrated for 40 examples comprising both 5- and 6-membered ring formations.
Calcium(II)-Catalyzed Intra- and Intermolecular Hydroamidation of Unactivated Alkenes in Hexafluoroisopropanol
Qi, Chenxiao,Hasenmaile, Felix,Gandon, Vincent,Leb?uf, David
, p. 1734 - 1739 (2018/03/13)
A combination of a calcium(II) triflimide salt and hexafluoroisopropanol (HFIP) was found to be a highly efficient promoter system for the intra- and intermolecular hydroamidation of unactivated alkenes. Unlike other methods, a vast array of functional groups is tolerated at the nitrogen and alkene moieties. The reaction produces the corresponding nitrogen-containing compounds in excellent yields and good diastereoselectivities. The use of HFIP as solvent proved crucial for the proper carrying out of this transformation. Its role, as well as that of calcium and its NTf2 ligand, was rationalized by DFT computations. These calculations show how the [(NTf2)Ca(HFIP)n]+ complex can activate the amide via a basic site of the NTf2 ligand and the alkene with one acidic HFIP proton. The acidity of HFIP is exacerbated by the coordination to the calcium center, the more so as n increases.
Piperidines from acid-catalysed cyclisations: Pitfalls, solutions and a new ring contraction to pyrrolidines
Aldmairi, Abdul H.,Griffiths-Jones, Charlotte,Dupauw, Alexis,Henderson, Laura,Knight, David W.
, p. 3690 - 3694 (2017/09/02)
The success of acid-catalysed cyclisations of alka-4-enylamine derivatives to piperidines depends very much on the nature of the amine protecting group: while carbamates and related amides can usually be readily and cleanly transformed, the corresponding sulfonamides react further by ring contraction leading to pyrrolidines, especially when such substrates are sterically crowded.