- Access to functionalized luminescent Pt(ii) complexes by photoredox-catalyzed Minisci alkylation of 6-aryl-2,2′-bipyridines
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Photoredox-mediated C-H bond alkylation of 6-aryl-2,2′-bipyridines withN-(acyloxy)phthalimides is reported. The reaction exhibits excellent functional group tolerance, including chiral aliphatic groups. The influence of the incorporatedC6′-alkyl group on
- Hagui, Wided,Cordier, Marie,Boixel, Julien,Soulé, Jean-Fran?ois
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supporting information
p. 1038 - 1041
(2021/02/06)
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- Decarboxylative Amination: Diazirines as Single and Double Electrophilic Nitrogen Transfer Reagents
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The ubiquity of nitrogen-containing small molecules in medicine necessitates the continued search for improved methods for C-N bond formation. Electrophilic amination often requires a disparate toolkit of reagents whose selection depends on the specific structure and functionality of the substrate to be aminated. Further, many of these reagents are challenging to handle, engage in undesired side reactions, and function only within a narrow scope. Here we report the use of diazirines as practical reagents for the decarboxylative amination of simple and complex redox-active esters. The diaziridines thus produced are readily diversifiable to amines, hydrazines, and nitrogen-containing heterocycles in one step. The reaction has also been applied in fluorous phase synthesis with a perfluorinated diazirine.
- Chandrachud, Preeti P.,Wojtas, Lukasz,Lopchuk, Justin M.
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supporting information
p. 21743 - 21750
(2021/01/11)
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- Radical Deuteration with D2O: Catalysis and Mechanistic Insights
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Selective incorporation of deuterium atoms into molecules is of high interest for labeling purposes and for optimizing properties of drug candidates. A mild and environmentally benign method for the deuteration of alkyl iodides via radical pathway using D2O as source of deuterium has been developed. The reaction is initiated and mediated by triethylborane in the presence of dodecanethiol as a catalyst. This method is compatible with a wide range of functional groups and provides the monodeuterated products in good yields and with a high level of deuterium incorporation. It opens promising opportunities for the development of enantioselective radical reactions. Moreover, a revision of the mechanism of the deoxygenation reaction of xanthates using R3B and water (Wood deoxygenation) is presented.
- Soulard, Valentin,Villa, Giorgio,Vollmar, Denis Patrick,Renaud, Philippe
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p. 155 - 158
(2018/01/17)
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- Decarboxylative radical azidation using MPDOC and MM DOC esters
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An efficient radical-mediated decarboxylative azidation of aliphatic carboxylic acids has been developed. The success of this transformation hinges on the use of a new type of thiohydroxamate esters (MPDOC esters). These esters are more stable than the cl
- Nyfeler, Erich,Renaud, Philippe
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supporting information; experimental part
p. 985 - 988
(2009/04/10)
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- Nitrilase-catalyzed enantioselective synthesis of pyrrolidine- And piperidinecarboxylic acids
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The enantioselective synthesis of the nonproteinogenic amino acids β-proline and nipecotic acids from their readily available nitriles is achieved in high enantiomeric excess by commercially available nitrilases. The presented procedure comprises not more than 4 steps, thus considerably reducing the multiple steps generally required. Amide formation is also observed for specific heterocyclic nitriles.
- Winkler, Margit,Meischler, Dorith,Klempier, Norbert
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p. 1475 - 1480
(2008/09/16)
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- Photochemical synthesis of highly functionalized cyclopropyl ketones
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A series of di- and trisubstituted cyclopropyl ketones 11 were prepared by irradiation of ketones 3 and 5, which bear a leaving group adjacent to the carbonyl C-atom. The required ketones 3 could be easily synthesized either by functionalization of ketones 1 with a hypervalent iodine reagent, 2, or by O-sulfonylation of α-hydroxy ketones 7. The nitrates 5 were obtained by treatment of the corresponding α-bromo ketones with AgNO3. The irradiation of 3 and 5 must be performed in the presence of an acid scavenger (1-methyl-1H-imidazole) to obtain the cyclopropanes 11 in good yields. The synthetic efficiency of the method was, among other things, demonstrated by the preparation of a highly strained bicyclo[2.1.0]pentane 11i in good yield. The mechanism of the photochemical cyclization was investigated by means of photokinetic measurements, as well as by quantum-chemical calculations. It was shown that the presence of the leaving group substantially influences all steps of the photochemical reaction cascade. The X-ray crystal structures of 11j and exo-11k were also determined.
- Wessig, Pablo,Muehling, Olaf
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p. 865 - 893
(2007/10/03)
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