Catalytic Hydrogen Atom Transfer (HAT) for Sustainable and Diastereoselective Radical Reduction

Gansäuer, Andreas; Klatte, Max; Brändle, Gerhard M.; Friedrich, Joachim

doi:10.1002/anie.201202818

Cited by 100 publications

(46 citation statements)

References 35 publications

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“…[1] In chain reactions,HAT has usually been carried out with Bu 3 SnH, [1] (Me 3 Si) 3 SiH, [2] or NHC-Boranes as stoichiometric H-atom donors. [4,5] An attractive alternative for HATc atalysis that does not require the use of H 2 is lowering of the bond dissociation energy (BDE) of molecules with strong OÀH bonds,such as H 2 OorCH 3 OH, by coordination to low-valent metal reagents,s uch as titanocene(III) complexes. [4,5] An attractive alternative for HATc atalysis that does not require the use of H 2 is lowering of the bond dissociation energy (BDE) of molecules with strong OÀH bonds,such as H 2 OorCH 3 OH, by coordination to low-valent metal reagents,s uch as titanocene(III) complexes.…”

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confidence: 99%

“…[3] With respect to sustainability,the use of HATcatalysts is clearly more attractive.T od ate,t he generation of such catalysts has relied on the in situ generation of metal complexes containing M À Hb onds generated from H 2 or silanes. [4,5] An attractive alternative for HATc atalysis that does not require the use of H 2 is lowering of the bond dissociation energy (BDE) of molecules with strong OÀH bonds,such as H 2 OorCH 3 OH, by coordination to low-valent metal reagents,s uch as titanocene(III) complexes. [6] However,t he titanocene reagent is often used in stoichiometric amounts.…”

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confidence: 99%

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Amide‐Substituted Titanocenes in Hydrogen‐Atom Transfer Catalysis

et al. 2015

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Two new catalytic systems for hydrogen-atom transfer (HAT) catalysis involving the N-H bonds of titanocene(III) complexes with pendant amide ligands are reported. In a monometallic system, a bifunctional catalyst for radical generation and reduction through HAT catalysis depending on the coordination of the amide ligand is employed. The pendant amide ligand is used to activate Crabtree's catalyst to yield an efficient bimetallic system for radical generation and HAT catalysis.

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Amide‐Substituted Titanocenes in Hydrogen‐Atom Transfer Catalysis

et al. 2015

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“…This is indeed the case for radical reduction and for acrylate addition at reflux in THF. Our recently described epoxide reduction (via intramolecular HAT from a TiH bond), which does not require the presence of Mn or 4 , is much faster than arylation (Scheme , last example) 23…”

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confidence: 99%

Application of Cationic Poly(lactic‐co‐glycolic acid) Iron Oxide/Chitosan‐Based Nanocomposite for the Determination of Paraoxon

2014

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The preparation of stable oleic‐acid‐capped iron‐oxide nanoparticles is reported, which were further coated with cationic poly (d,l‐lactic‐co‐glycolic acid) and chitosan in aqueous media by using a nano‐emulsion technique. The prepared composite was used to modify a glassy carbon electrode and the electrochemical behavior and stability of modified electrode were investigated by using cyclic voltammetry. This platform was then utilized to prepare an electrochemical pesticide biosensor based on the inhibition study of the enzyme acetylcholinesterase. Furthermore, the response characteristics show that this fabricated electrode has a shelf life of about 3–4 months and has good adhesion properties along with homogeneous dispersion at the electrode surface. The linear range and detection limit for paraoxon pesticide detection was found to be 9.55–37.1 nM and 8.91 nM, respectively.

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“…Gansäuer and co‐workers reported a titanium(III) hydride promoted diastereoselective hydrosilylation of epoxides with PhMeSiH 2 . Ti III −H species 6 was conveniently in situ generated through the reaction of either [{Cp 2 TiOC 2 H 5 } 2 ] or [Ti(CH 3 ) 2 Cp 2 ] as precatalysts with excess PhMeSiH 2 (Scheme ).…”

Section: Hydrosilylative Reduction Of Epoxidesmentioning

confidence: 99%

Catalytic Reduction of Cyclic Ethers with Hydrosilanes

Park

2019

Chemistry An Asian Journal

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Catalytic reductive transformations of ethers as a synthetic building block are an important class of chemical reactions because a range of essential chemical feedstocks and fuels in contemporary life can be prepared through the key step of ethereal C−O bond cleavage of cellulosic biomass. Although conventional stoichiometric and catalytic methods for sp2‐ and sp3‐C−O bond cleavage of linear ethers and alcohols with hydrosilanes are well established, silylative ring opening of cyclic ethers has been less highlighted in this context. This review outlines catalytic systems for the silylative reduction of a range of cyclic ethers, including epoxides and sugars, leading to the corresponding alcohols and/or hydrocarbons. The chemical reactivity and selectivity of these ring‐opening catalytic processes are discussed with respect to the type of substrates; the representative catalytic working modes are also described.

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Catalytic Hydrogen Atom Transfer (HAT) for Sustainable and Diastereoselective Radical Reduction

Cited by 100 publications

References 35 publications

Amide‐Substituted Titanocenes in Hydrogen‐Atom Transfer Catalysis

Amide‐Substituted Titanocenes in Hydrogen‐Atom Transfer Catalysis

Application of Cationic Poly(lactic‐co‐glycolic acid) Iron Oxide/Chitosan‐Based Nanocomposite for the Determination of Paraoxon

Catalytic Reduction of Cyclic Ethers with Hydrosilanes

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