13610-03-2Relevant academic research and scientific papers
Photochemical Doyle-Kirmse Reaction: A Route to Allenes
Or?owska, Katarzyna,Rybicka-Jasińska, Katarzyna,Krajewski, Piotr,Gryko, Dorota
supporting information, p. 1018 - 1021 (2020/01/31)
This Letter describes the metal-free, blue-light-induced [2,3]-sigmatropic rearrangement of sulfonium ylides generated from donor/acceptor diazoalkanes and propargyl sulfides. The reaction furnishes highly functionalized allenes from a broad range of starting materials in decent yield. Mechanistic experiments supported by the literature data suggest singlet carbenes as intermediates in this reaction.
Intermolecular Pummerer Coupling with Carbon Nucleophiles in Non-Electrophilic Media
Colas, Kilian,Martín-Montero, Raúl,Mendoza, Abraham
supporting information, p. 16042 - 16046 (2017/11/21)
A new Pummerer-type C?C coupling protocol is introduced based on turbo-organomagnesium amides, which unlike traditional Pummerer reactions, does not require strong electrophilic activators, engages a broad range of C(sp3)-, C(sp2)-, and C(sp)-nucleophiles, and seamlessly integrates with C?H and C?X magnesiation. Given the central character of sulfur compounds in organic chemistry, this protocol allows access to unrelated carbonyls, olefins, organometallics, halides, and boronic esters through a single strategy.
Catalytic activation of diazo compounds using electron-rich, defined iron complexes for carbene-transfer reactions
Holzwarth, Michael S.,Alt, Isabel,Plietker, Bernd
supporting information; experimental part, p. 5351 - 5354 (2012/07/14)
Carbene transfer: The electron-rich iron complex Bu4N[Fe(CO) 3(NO)] efficiently catalyzes different carbene-transfer reactions. Various diazo compounds can be used. The high stability of the employed iron complexes is demonstrated by the generation of the diazo reagent in situ and a sequential iron-catalyzed allylic sulfenylation/Doyle-Kirmse reaction. Copyright
Reduction of propargylic sulfones to (Z)-allylic sulfones using zinc and ammonium chloride
Sheldrake, Helen M.,Wallace, Timothy W.
, p. 4407 - 4411 (2008/02/03)
Propargylic sulfones can be cis-hydrogenated using commercial zinc powder and ammonium chloride in THF-water at room temperature, the major products being the corresponding (Z)-allylic sulfones. Other reducible groups (alkene, benzyloxy) are not affected. Allenylsulfones are implicated in one of the possible reaction pathways.
Iron(II)-catalyzed sulfimidation and [2,3]-sigmatropic rearrangement of propargyl sulfides with tert-butoxycarbonyl azide. Access to N-allenylsulfenimides
Bacci, James P.,Greenman, Kevin L.,Van Vranken, David L.
, p. 4955 - 4958 (2007/10/03)
The iron(II)-catalyzed Bach reaction of tert-butoxycarbonyl azide (BocN3) and allyl sulfides has been extended to include propargyl sulfides, which give N-allenylsulfenimide products. Using 10 mol % dppeFeCl2 as catalyst the reaction
Amination and [2,3]-sigmatropic rearrangement of propargylic sulfides using a ketomalonate-derived oxaziridine: synthesis of N-allenylsulfenimides.
Armstrong, Alan,Cooke, Richard S,Shanahan, Stephen E
, p. 3142 - 3143 (2007/10/03)
Amination of propargylic sulfides with a ketomalonate-derived oxaziridine under metal free conditions gives N-Boc-N-allenylsulfenimides via [2,3]-sigmatropic rearrangement.
Ruthenium-catalyzed S-propargylation of thiols enables the rapid synthesis of propargylic sulfides
Kondo, Teruyuki,Kanda, Yusuke,Baba, Atsushi,Fukuda, Kenji,Nakamura, Ayako,Wada, Kenji,Morisaki, Yasuhiro,Mitsudo, Take-aki
, p. 12960 - 12961 (2007/10/03)
A new and highly efficient catalytic system based on CpRuClL2 is proposed for the S-propargylation of thiols by propargylic carbonates under neutral conditions, in which specific requirements inherent to the different reactivities of aliphatic and aromatic thiols are achieved by tuning both the nature of the ancillary ligand L and the experimental conditions. Copyright
