82303-13-7Relevant academic research and scientific papers
Sequential Organozinc Formation and Negishi Cross-Coupling of Amides Catalysed by Cobalt Salt
Dorval, Céline,Dubois, Elodie,Bourne-Branchu, Yann,Gosmini, Corinne,Danoun, Grégory
supporting information, p. 1777 - 1780 (2019/02/26)
Herein, a cobalt-catalysed Negishi-type cross-coupling of amide derivatives is described. Apart from being the first example of cobalt-catalysed Negishi-type coupling of amides, the process described employs a unique, simple, and cheap catalytic system to perform both the organozinc formation and the Negishi-type coupling. Indeed, the same cobalt(II) bromide salt used to form the arylzinc species from aryl bromides is then re-used to perform the cross coupling of this resulting arylzinc with N-benzoyl glutarimides at room temperature. The main advantages of the reaction presented are its robustness and ease of use. Indeed, the reactions of organozinc formation and Negishi-type coupling are performed without precautions toward water or oxygen. (Figure presented.).
Generation and Cross-Coupling of Organozinc Reagents in Flow
Herath, Ananda,Molteni, Valentina,Pan, Shifeng,Loren, Jon
supporting information, p. 7429 - 7432 (2019/01/03)
A versatile flow synthesis method for in situ formation of organozinc reagents and subsequent cross-coupling with aryl halides and activated carboxylic acids is reported. Formation of organozinc reagents is achieved by pumping organic halides, in the presence of ZnCl2 and LiCl, through an activated Mg-packed column under flow conditions. This method provides efficient in situ formation of aryl, primary, secondary, and tertiary alkyl organozinc reagents, which are subsequently telescoped downstream to a Negishi or decarboxylative Negishi cross-coupling reaction. The described method offers access to a variety of C-C bond formations with organozinc reagents that are otherwise commercially unavailable or difficult to prepare under traditional batch reaction conditions.
Cobalt-Catalyzed Formation of 2-Pyridylzinc Reagents and Their Subsequent Coupling
Linke, Stephanie,Manolikakès, Sofia M.,Auffrant, Audrey,Gosmini, Corinne
, p. 2595 - 2600 (2018/06/08)
The preparation of pyridylzinc compounds from the corresponding pyridyl halides using a cobalt catalyst is described. The complex employed features a polydentate N-heterocyclic ligand and allows the reaction to be carried out in the absence of pyridine as
Cobalt-Catalyzed Oxidative Homocoupling of Arylzinc Species
Bourne-Branchu, Yann,Moncomble, Aurélien,Corpet, Martin,Danoun, Gregory,Gosmini, Corinne
, p. 3352 - 3356 (2016/09/12)
A novel procedure for the synthesis of functionalized symmetrical biaryl compounds is described. The reaction proceeds via the oxidative homocoupling of arylzinc species formed by cobalt catalysis in the presence of air or p-benzoquinone depending on the nature of the functional group.
N-protected 1,2-oxazetidines as a source of electrophilic oxygen: Straightforward access to benzomorpholines and related heterocycles by using a reactive tether
Javorskis, Tomas,Sriubaite, Simona,Bagd?iunas, Gintautas,Orentas, Edvinas
supporting information, p. 9157 - 9164 (2015/06/16)
A hitherto unknown reactivity of a strained four-membered heterocycle, 1,2-oxazetidine, is reported. When reacted with organometallic compounds, this reagent provides electrophilic oxygen with a nitrogen-terminated two-carbon-atom tether. The synthetic versatility of the products obtained was demonstrated in various transformations, leading to efficient synthesis of six-, seven-, and eight-membered heterocyclic systems of pharmaceutical importance. Open and then close: The O-selective ring-opening reaction of 1,2-oxazetidines with organometallic compounds provides tethered phenol derivatives that can be used to access six-, seven-, and eight-membered heterocyclic systems in only a few steps (see scheme; Ts=tosyl).
Nickel-catalyzed enantioselective arylation of pyridinium ions: Harnessing an iminium ion activation mode
Chau, Stephen T.,Lutz, J. Patrick,Wu, Kevin,Doyle, Abigail G.
supporting information, p. 9153 - 9156 (2013/09/12)
A nickel for your thoughts.?? An enantioselective nickel-catalyzed cross-coupling between N-acylpyridinium salts and organozinc reagents is reported. The catalytic system, which is comprised of an air-stable NiII source and a chiral phosphoramidite ligand, affords 2-substituted-2,3-dihydro-4-pyridones with up to >99 % ee. Copyright
Directed nickel-catalyzed negishi cross coupling of alkyl aziridines
Nielsen, Daniel K.,Huang, Chung-Yang,Doyle, Abigail G.
supporting information, p. 13605 - 13609 (2013/09/24)
Herein we report a nickel-catalyzed C-C bond-forming reaction between simple alkyl aziridines and organozinc reagents. This method represents the first catalytic cross-coupling reaction employing a nonallylic and nonbenzylic Csp3-N bond as an electrophile. Key to its success is the use of a new N-protecting group (cinsyl or Cn) bearing an electron-deficient olefin that directs oxidative addition and facilitates reductive elimination. Studies pertinent to elucidation of the mechanism of cross coupling are also presented.
Cobalt-catalyzed electrophilic amination of arylzincs with N-chloroamines
Qian, Xin,Yu, Zailu,Auffrant, Audrey,Gosmini, Corinne
supporting information, p. 6225 - 6229 (2013/07/05)
Roles reversed: An efficient cobalt-catalyzed electrophilic amination of arylzinc reagents has been achieved. A variety of functionalized arylzincs and N-chloroamines were coupled under mild conditions (see scheme). Both secondary and tertiary arylamines were obtained in moderate to excellent yields. Copyright
Cobalt-catalysed synthesis of highly substituted styrene derivatives via arylzincation of alkynes
Corpet, Martin,Gosmini, Corinne
supporting information, p. 11561 - 11563,3 (2012/12/12)
A new two-step procedure was developed by carbozincation of internal and terminal alkynes to synthesise highly functionalised vinylzinc bromides. Various tri and tetrasubstituted alkenes were prepared in moderate to good yields under mild reaction conditions in a stereo-selective manner. This methodology represents an interesting alternative to previously known methods. This journal is
