A heterogeneous layered bifunctional catalyst for the integration of aerobic oxidation and asymmetric C–C bond formation

2013 ◽  
Vol 49 (85) ◽  
pp. 9917 ◽  
Author(s):  
Hiroyuki Miyamura ◽  
Gerald C. Y. Choo ◽  
Tomohiro Yasukawa ◽  
Woo-Jin Yoo ◽  
Shu Kobayashi
ChemInform ◽  
2014 ◽  
Vol 45 (8) ◽  
pp. no-no
Author(s):  
Hiroyuki Miyamura ◽  
Gerald C. Y. Choo ◽  
Tomohiro Yasukawa ◽  
Woo-Jin Yoo ◽  
Shu Kobayashi

Synthesis ◽  
2018 ◽  
Vol 51 (02) ◽  
pp. 450-462 ◽  
Author(s):  
Chris Dockendorff ◽  
Eric Greve ◽  
Jacob Porter

Bifunctional catalyst systems for the direct addition of ­ketones to unactivated alkenes/alkynes were designed and modeled by density functional theory (DFT). The designed catalysts possess bidentate ligands suitable for binding of pi-acidic group 10 metals capable of activating alkenes/alkynes, and a tethered organocatalyst amine to ­activate the ketone via formation of a nucleophilic enamine intermediate. The structures of the designed catalysts before and after C–C bond formation were optimized using DFT, and reaction steps involving group 10 metals were predicted to be significantly exergonic. A novel oxazoline precatalyst with a tethered amine separated by a meta-substituted benzene spacer was synthesized via a 10-step sequence that ­includes a key regioselective epoxide ring-opening step. It was combined with group 10 metal salts, including cationic Pd(II) and Pt(II), and screened for the direct addition of ketones to several alkenes and an ­internal alkyne. 1H NMR studies suggest that catalyst-catalyst inter­actions with this system via amine–metal coordination may preclude the desired addition reactions. The catalyst design approach disclosed here, and the promising calculations obtained with square planar group 10 metals, light a path for the discovery of novel bifunctional catalysts for C–C bond formation.


2018 ◽  
Vol 16 (23) ◽  
pp. 4236-4242 ◽  
Author(s):  
Hai Huang ◽  
Jeffrey Ash ◽  
Jun Yong Kang

Base-controlled Fe(Pc)-catalyzed S–S/S–P(O) bond formation.


2014 ◽  
Vol 50 (23) ◽  
pp. 3036-3039 ◽  
Author(s):  
Fengrui Qu ◽  
Julia R. Khusnutdinova ◽  
Nigam P. Rath ◽  
Liviu M. Mirica

An isolable Pd(iv)–OH complex formed upon aerobic oxidation of an organometallic Pd(ii) precursor exhibits selective C(sp2)–O bond formation reactivity.


2014 ◽  
Vol 50 (58) ◽  
pp. 7855-7857 ◽  
Author(s):  
Mojtaba Mahyari ◽  
Mohammad Sadegh Laeini ◽  
Ahmad Shaabani

Copper(ii) tetrasulfophthalocyanine supported on three-dimensional nitrogen-doped graphene-based frameworks was synthesized and introduced as a bifunctional catalyst for selective aerobic oxidation of alkyl arenes and alcohols.


2017 ◽  
Vol 8 (2) ◽  
pp. 1356-1359 ◽  
Author(s):  
Hong-Gang Cheng ◽  
Javier Miguélez ◽  
Hiroyuki Miyamura ◽  
Woo-Jin Yoo ◽  
Shū Kobayashi

A chiral heterogeneous material was prepared and evaluated as a bifunctional catalyst for the sequential aerobic oxidation-asymmetric intramolecular aza-Friedel–Crafts reaction.


Catalysts ◽  
2020 ◽  
Vol 10 (6) ◽  
pp. 712
Author(s):  
Jiequn Wu ◽  
Weiming Hua ◽  
Yinghong Yue ◽  
Zi Gao

A highly efficient bifunctional catalyst of an s-triazine-based carbon-nitride-supported cobalt oxide is developed for the aerobic oxidation–Knoevenagel condensation tandem reaction of benzyl alcohol and malononitrile, whereby 96.4% benzyl alcohol conversion with nearly 100% selectivity towards benzylmalononitrile can be obtained in 6 h at 80 °C. The excellent catalytic performance derives from the high basicity of carbon nitride and strong redox ability of Co species induced by carbon nitride. The catalyst is also quite stable and can be reused without any regeneration treatment, whose product yield is only an 11.5% reduction after four runs.


2012 ◽  
Vol 18 (17) ◽  
pp. 5170-5174 ◽  
Author(s):  
Magnus Rueping ◽  
René M. Koenigs ◽  
Konstantin Poscharny ◽  
David C. Fabry ◽  
Daniele Leonori ◽  
...  

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