A Formally Zwitterionic Ruthenium Catalyst Precursor for the Transfer Hydrogenation of Ketones that Does Not Feature an Ancillary Ligand NH Functionality

2007 ◽  
Vol 119 (25) ◽  
pp. 4816-4819 ◽  
Author(s):  
Rylan J. Lundgren ◽  
Matthew A. Rankin ◽  
Robert McDonald ◽  
Gabriele Schatte ◽  
Mark Stradiotto
ChemInform ◽  
2007 ◽  
Vol 38 (40) ◽  
Author(s):  
Rylan J. Lundgren ◽  
Matthew A. Rankin ◽  
Robert McDonald ◽  
Gabriele Schatte ◽  
Mark Stradiotto

2007 ◽  
Vol 46 (25) ◽  
pp. 4732-4735 ◽  
Author(s):  
Rylan J. Lundgren ◽  
Matthew A. Rankin ◽  
Robert McDonald ◽  
Gabriele Schatte ◽  
Mark Stradiotto

Molecules ◽  
2021 ◽  
Vol 26 (4) ◽  
pp. 1165
Author(s):  
Yasuhiro Sato ◽  
Yuichi Kawata ◽  
Shungo Yasui ◽  
Yoshihito Kayaki ◽  
Takao Ikariya

As a candidate for bifunctional asymmetric catalysts containing a half-sandwich C–N chelating Ir(III) framework (azairidacycle), a dinuclear Ir complex with an axially chiral linkage is newly designed. An expedient synthesis of chiral 2,2′-bis(aminomethyl)-1,1′-binaphthyl (1) from 1,1-bi-2-naphthol (BINOL) was accomplished by a three-step process involving nickel-catalyzed cyanation and subsequent reduction with Raney-Ni and KBH4. The reaction of (S)-1 with an equimolar amount of [IrCl2Cp*]2 (Cp* = η5–C5(CH3)5) in the presence of sodium acetate in acetonitrile at 80 °C gave a diastereomeric mixture of new dinuclear dichloridodiiridium complexes (5) through the double C–H bond cleavage, as confirmed by 1H NMR spectroscopy. A loss of the central chirality on the Ir centers of 5 was demonstrated by treatment with KOC(CH3)3 to generate the corresponding 16e amidoiridium complex 6. The following hydrogen transfer from 2-propanol to 6 provided diastereomers of hydrido(amine)iridium retaining the bis(azairidacycle) architecture. The dinuclear chlorido(amine)iridium 5 can serve as a catalyst precursor for the asymmetric transfer hydrogenation of acetophenone with a substrate to a catalyst ratio of 200 in the presence of KOC(CH3)3 in 2-propanol, leading to (S)-1-phenylethanol with up to an enantiomeric excess (ee) of 67%.


Synlett ◽  
2019 ◽  
Vol 30 (04) ◽  
pp. 503-507 ◽  
Author(s):  
Jacob Schneekönig ◽  
Kathrin Junge ◽  
Matthias Beller

The asymmetric transfer hydrogenation of ketones using isopropyl alcohol (IPA) as hydrogen donor in the presence of novel manganese catalysts is explored. The selective and active systems are easily generated in situ from [MnBr(CO)5] and inexpensive C 2-symmeric bisoxalamide ligands. Under the optimized reaction conditions, the Mn-derived catalyst gave higher enantioselectivity compared with the related ruthenium catalyst.


2011 ◽  
Vol 30 (23) ◽  
pp. 6339-6342 ◽  
Author(s):  
Ismael Nieto ◽  
Michelle S. Livings ◽  
John B. Sacci ◽  
Lauren E. Reuther ◽  
Matthias Zeller ◽  
...  

ChemPlusChem ◽  
2016 ◽  
Vol 81 (6) ◽  
pp. 541-549 ◽  
Author(s):  
Yinzheng Xie ◽  
Mengpan Wang ◽  
Xiaohui Wu ◽  
Chen Chen ◽  
Wenbo Ma ◽  
...  

ACS Catalysis ◽  
2019 ◽  
Vol 9 (12) ◽  
pp. 11302-11306 ◽  
Author(s):  
Lorenz Pardatscher ◽  
Benjamin J. Hofmann ◽  
Pauline J. Fischer ◽  
Sebastian M. Hölzl ◽  
Robert M. Reich ◽  
...  

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