ChemInform Abstract: Low-Temperature Formation of Functionalized Grignard Reagents from Direct Oxidative Addition of Active Magnesium to Aryl Bromides.

ChemInform ◽  
2000 ◽  
Vol 31 (48) ◽  
pp. no-no
Author(s):  
Jun-sik Lee ◽  
Raffet Velarde-Ortiz ◽  
Albert Guijarro ◽  
Joshua R. Wurst ◽  
Reuben D. Rieke
Keyword(s):  
Low Temperature ◽  
Oxidative Addition ◽  
Grignard Reagents ◽  
Aryl Bromides

Low-Temperature Formation of Functionalized Grignard Reagents from Direct Oxidative Addition of Active Magnesium to Aryl Bromides

2000 ◽  
Vol 65 (17) ◽  
pp. 5428-5430 ◽  
Author(s):  
Jun-sik Lee ◽  
Raffet Velarde-Ortiz ◽  
Albert Guijarro ◽  
Reuben D. Rieke
Keyword(s):  
Low Temperature ◽  
Oxidative Addition ◽  
Grignard Reagents ◽  
Aryl Bromides

scholarly journals Microwave-assisted Efficient Synthesis of Alliodorin and (±)-Curcuhydroquinone

1999 ◽  
Vol 23 (2) ◽  
pp. 164-165
Author(s):  
Goverdhan L. Kad ◽  
Anupam Khurana ◽  
Vasundhara Singh ◽  
Jasvinder Singh
Keyword(s):  
Grignard Reagents ◽  
Methyl Groups ◽  
Efficient Synthesis ◽  
Alkyl Aryl ◽  
Microwave Assisted ◽  
Aryl Bromides ◽  
Key Steps

Terpenoids 1 and 2 have been synthesized from readily available starting materials using Li2CuCI4-catalysed coupling of Grignard reagents with alkyl/aryl bromides and microwave-assisted oxidation of allylic methyl groups, using SeO2/ButOOH adsorbed over SiO2 as key steps.

scholarly journals H2 Evolution from H2O via O–H Oxidative Addition Across a 9,10-Diboraanthracene

2020 ◽  
Author(s):  
Jordan W. Taylor ◽  
William Harman
Keyword(s):  
Low Temperature ◽  
Lewis Acids ◽  
31P Nmr ◽  
Variable Temperature ◽  
Oxidative Addition ◽  
H2 Evolution ◽  
Chloride Exchange ◽  
11B Nmr

The boron-centered water reactivity of the boroauride complex ([Au(B2P2)][K(18-c-6)]; (B2P2, 9,10-bis(2-(diisopropylphosphino)- phenyl)-9,10-dihydroboranthrene) and its corresponding twoelectron oxidized complex, Au(B2P2)Cl, are presented. The tolerance of Au(B2P2)Cl towards H2O was demonstrated and subsequent hydroxide/chloride exchange was acheived in the presence of H2O and triethylamine to afford Au(B2P2)OH. Au(B2P2)]Cl and [Au(B2P2)]OH are poor Lewis acids as judged by the Gutmann-Becket method, with [Au(B2P2)]OH displaying facile hydroxide exchange between B atoms of the DBA ring as evidenced by variable temperature 31P NMR and low temperature 1H and 11B NMR. The reaction of the reduced boroauride complex [Au(B2P2)]– with 1 equivalent of H2O produces a hydride/hydroxide product, [Au(B2P2)(H)(OH)]–, that, upon addition of a second equivalent of H2O, rapidly evolves H2 to yield the dihydroxide compound, [Au(B2P2)(OH)2]–. [Au(B2P2)]Cl can be regenerated from [Au(B2P2)(OH)2]– via HCl·Et2O, providing a synthetic cycle for H2 evolution from H2O enabled by O–H oxidative addition at a diboraanthracene unit.

scholarly journals Oxidative Addition of Aryl Halides to a Ni(I)-Bipyridine Complex

2022 ◽  
Author(s):  
Stephen Ting ◽  
Wendy Williams ◽  
Abigail Doyle
Keyword(s):  
Oxidative Addition ◽  
Aryl Halides ◽  
Solution Phase ◽  
Nickel Catalysis ◽  
Mechanistic Studies ◽  
Redox Equilibrium ◽  
Aryl Bromides ◽  
First Time

The oxidative addition of aryl halides to bipyridine- or phenanthroline-ligated nickel(I) is a commonly proposed step in nickel catalysis. However, there is a scarcity of complexes of this type that both are well-defined and undergo oxidative addition with aryl halides, hampering organometallic studies of this process. We report the synthesis of a well-defined Ni(I) complex, [(CO2Etbpy)NiCl]4 (1). Its solution-phase speciation is characterized by a significant population of monomer and a redox equilibrium that can be perturbed by π-acceptors and σ-donors. 1 reacts readily with aryl bromides, and mechanistic studies are consistent with a mechanism proceeding through an initial Ni(I) → Ni(III) oxidative addition. Such a process was demonstrated stoichiometrically for the first time, affording a structurally characterized Ni(III) aryl complex.

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