- Chain extension of aldonolactones by samarium iodide mediated Dreiding- Schmidt reactions and samarium assisted Imamoto reactions
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Unprecedented SmI2 mediated Dreiding-Schmidt reactions were used for chain extension reactions of aldonolactones with alkyl 2-bromomethyl acrylates or 2-bromomethyl-acrylonitrile, respectively. The reaction of aldonolactones with diiodomethane
- Csuk, Rene,Hoering, Ulrike,Schaade, Martina
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- Copper-catalyzed radical oxyallylation of olefins for the construction of alkene-containing isoxazolines
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A radical-mediated approach to alkene oxyallylation using allylic oximes is described. The reaction proceeds under copper-catalytic redox-neutral conditions and tolerates various functional groups. This protocol thus enables the synthesis of structurally valuable isoxazolines and the introduction of a versatile olefin motif in a single step.
- He, Xiaoxue,Qian, Lijie,Dai, Yuyu,Yan, Xinhuan,Li, Xiaoqing,Xu, Xiangsheng
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supporting information
(2021/05/31)
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- Copper-Catalyzed Intermolecular Alkynylation and Allylation of Unactivated C(sp3)-H Bonds via Hydrogen Atom Transfer
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We describe Cu-catalyzed intermolecular alkynylation and allylation of unactivated C(sp3)-H bonds with singly occupied molecular orbital-philes (SOMO-philes) via hydrogen atom transfer (HAT). Employing N-fluoro-sulfonamide as a HAT reagent, a set of subst
- Liang, Lei,Guo, Ge,Li, Chen,Wang, Song-Lin,Wang, Yue-Hui,Guo, Hai-Ming,Niu, Hong-Ying
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supporting information
p. 8575 - 8579
(2021/11/13)
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- Photoredox-Coupled F-Nucleophilic Addition: Allylation of gem-Difluoroalkenes
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A novel strategy for the expedient construction of CF3-embeded tertiary/quarternary carbon centers was developed by taking advantage of photoredox catalysis. Thanks to a key step of single-electron oxidation, electron-rich gem-difluoroalkenes, which otherwise are essentially reluctant towards F-nucleoplilic addition, now readily participate in this fluoroallylation reaction. Furthermore, this strategy provides an elegant example for the generation, as well as functionalization, of α-CF3-substituted benzylic radical intermediates using cheap and readily available starting materials.
- Liu, Haidong,Ge, Liang,Wang, Ding-Xing,Chen, Nan,Feng, Chao
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supporting information
p. 3918 - 3922
(2019/02/19)
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- Intermolecular Aminoallylation of Alkenes Using Allyl-Oxyphthalimide Derivatives: A Case Study in Radical Polarity Effects
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A case study on the polarity effects of radical mediated intermolecular alkene aminoallylation is presented herein. This radical group transfer method pairs vinyl ethers with electronically deficient allyl-oxyphthalimide derivatives to give difunctionalized products while illustrating the guiding effects of polarity on this radical reactivity.
- Lardy, Samuel W.,Schmidt, Valerie A.
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supporting information
p. 6796 - 6799
(2019/11/03)
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- Gram-Scale Synthesis of the (?)-Sparteine Surrogate and (?)-Sparteine
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An 8-step, gram-scale synthesis of the (?)-sparteine surrogate (22 % yield, with just 3 chromatographic purifications) and a 10-step, gram-scale synthesis of (?)-sparteine (31 % yield) are reported. Both syntheses proceed with complete diastereocontrol and allow access to either antipode. Since the syntheses do not rely on natural product extraction, our work addresses long-term supply issues relating to these widely used chiral ligands.
- Firth, James D.,Canipa, Steven J.,Ferris, Leigh,O'Brien, Peter
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supporting information
p. 223 - 226
(2017/12/29)
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- FREE-STANDING NON-FOULING POLYMERS, THEIR COMPOSITIONS, AND RELATED MONOMERS
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Free-standing non-fouling polymers and polymeric compositions, monomers and macromonomers for making the polymers and polymeric compositions, objects made from the polymers and polymeric compositions, and methods for making and using the polymers and polymeric compositions.
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Page/Page column 42; 43
(2017/01/23)
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- C-H Bond Functionalization with the Formation of a C-C Bond: A Free Radical Condensation Reaction Based on the Phthalimido-N-oxyl Radical
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The development of a new chemical process that effects the conversion RH + C=C-C-X → R-C-C=C + HX, in which X is the phthalimido-N-oxyl radical (PINO·), is reported. The reaction yields are high, mass balances are excellent, and C-H bond functionalization and C-C bond formation are achieved in a single transformation. The byproduct of the reaction, N-hydroxyphthalimide, precipitates from solution and can be easily removed by simple filtration (and recycled). The kinetic chain lengths are shorter and the reaction times are longer (relative to those of the analogous reactions of allyl bromides), most likely because PINO· is a less-reactive hydrogen-atom abstractor. There appears to be no significant difference in efficiency in the addition-elimination steps. Competition experiments reveal that Br· and PINO· are comparable in leaving group ability.
- Patil, Shradha,Chen, Liang,Tanko, James M.
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supporting information
p. 502 - 505
(2015/10/05)
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- Regioselective radical bromoallylation of allenes leading to 2-bromo-substituted 1,5-dienes
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The regioselective radical bromoallylation of allenes proceeded efficiently in the presence of AIBN as a radical initiator to give 2-bromo-substituted 1,5-dienes in excellent yields. The addition of a bromine radical took place regioselectively onto the central carbon of allenes generating a stable allyl radical, which underwent addition/β-fragmentation reactions with allylbromides. The products could be further functionalized by Pd-catalyzed coupling reactions.
- Kippo, Takashi,Fukuyama, Takahide,Ryu, Ilhyong
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supporting information; experimental part
p. 3864 - 3867
(2011/09/15)
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- Unexpected electrophilic rearrangements of amides: A stereoselective entry to challenging substituted lactones
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"Chemical Equation Presented" Surprise, surprise! An unexpected skeletal rearrangement was developed into a chemo- and stereoselective synthesis of aallyl and allenyl lactones with challenging substitution patterns (see scheme; EWC = electron-withdrawing group). The generality, unique features, and synthetic potential of this reaction were probed and a mechanism was proposed.
- Madelaine, Claire,Valerio, Viviana,Maulide, Nuno
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supporting information; experimental part
p. 1583 - 1586
(2010/06/15)
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- Reactions of a Glycidyl Radical Equivalent with 2-Functionalised Allyl Stannates
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Reaction of 2-bromo-N-benzoylglycine methyl ester with 2-functionalised allyl stannane reagents under radical conditions provides a new route to α-alkylated amino acids in good yield, as exemplified by the facile synthesis of 4-methylene glutamate.
- Baldwin, Jack S.,Adlington, Robert M.,Lowe, Christopher,O'Neil, Ian A.,Sanders, Gillian L.,et al.
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p. 1030 - 1031
(2007/10/02)
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