13139-86-1Relevant articles and documents
Biaryls made easy: PEPPSI and the Kumada-Tamao-Corriu reaction
Organ, Michael G.,Abdel-Hadi, Mirvat,Avola, Stephanie,Hadei, Niloufar,Nasielski, Joanna,O'Brien, Christopher J.,Valente, Cory
, p. 150 - 157 (2007)
An easily employed, highly versatile Kumada-Tamao-Corriu (KTC) protocol utilizing the PEPPSI (Pyridine, Enhanced, Precatalyst, Preparation, Stabilization and Initiation) precatalysts 1 and 2 is detailed. The ease-of-use of these catalysts and the synthesis of a wide range of hindered biaryls, large coupling partners and drug-like heterocycles, in high yield, makes the PEPPSI-KTC protocol very attractive. The high reactivity of the PEPPSI system allowed a tetra-ortho substituted heterocycle, 11 to be synthesized at room temperature for the first time using any protocol. The PEPPSI protocols also tolerated the Boc protecting group and phenols required no protection in modified conditions. A relatively large scale (10g) reaction was also performed with no loss in performance. Furthermore, PEPPSI IPr, 1, was compared to previously reported highly active phosphine ligands 42, 43, and 44 and was shown to result in significantly better yields under identical conditions. Finally, we demonstrated that the PEPPSI catalyst system is very adept at performing sequential KTC coupling reactions, analogous to multicomponent reactions, which allow complex polyaryl and polyheteroaryl architectures to be produced in one single operation.
Processes for the Preparation of Zuclomiphene and Intermediates Thereof
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Paragraph 0140-0141, (2021/05/21)
The present invention provides processes for the preparation of zuclomiphene, as well as intermediates useful in the preparation thereof. In particular, processes are provided for the carbometallation of diphenylacetylene with a compound of Formula (3) to afford either zuclomiphene or an intermediate which is converted to zuclomiphene.
Strain-Promoted 1,3-Dithiolium-4-olates–Alkyne Cycloaddition
Kumar, Ramar Arun,Pattanayak, Manas R.,Yen-Pon, Expédite,Eliyan, Jijy,Porte, Karine,Bernard, Sabrina,Riomet, Margaux,Thuéry, Pierre,Audisio, Davide,Taran, Frédéric
supporting information, p. 14544 - 14548 (2019/09/17)
Reported here is the reactivity of mesoionic 1,3-dithiolium-4-olates towards strained alkynes, leading to thiophene cycloaddition products. In the process, the potential of these dipoles towards orthogonal reaction with azides, allowing efficient double ligation reactions, was discovered. A versatile process to access benzo[c]thiophenes, in an unprecedented divergent fashion, was developed and provides a new entry to unconventional polyaromatic thiophenes.
Nickel-Catalyzed Cross-Coupling of Functionalized Organo manganese Reagents with Aryl and Heteroaryl Halides Promoted by 4-Fluorostyrene
Benischke, Andreas D.,Desaintjean, Alexandre,Juli, Thomas,Cahiez, Gérard,Knochel, Paul
supporting information, p. 5396 - 5412 (2017/12/14)
A catalytic system consisting of Ni(acac) 2 (5 mol%) and 4-fluorostyrene (20 mol%) allows a convenient cross-coupling of functionalized organomanganese reagents with a variety of aryl and heteroaryl halides leading to polyfunctionalized diaryl- and arylheteroarylmethane derivatives.
