scholarly journals Alkynes as Allylmetal Equivalents in Redox-Triggered C–C Couplings to Primary Alcohols: (Z)-Homoallylic Alcohols via Ruthenium-Catalyzed Propargyl C–H Oxidative Addition

2014 ◽  
Vol 136 (34) ◽  
pp. 11902-11905 ◽  
Author(s):  
Boyoung Y. Park ◽  
Khoa D. Nguyen ◽  
Mani Raj Chaulagain ◽  
Venukrishnan Komanduri ◽  
Michael J. Krische
Keyword(s):  
Oxidative Addition ◽  
Primary Alcohols ◽  
Homoallylic Alcohols

ChemInform Abstract: Alkynes as Allylmetal Equivalents in Redox-Triggered C-C Couplings to Primary Alcohols: (Z)-Homoallylic Alcohols via Ruthenium-Catalyzed Propargyl C-H Oxidative Addition.

ChemInform ◽  
2015 ◽  
Vol 46 (11) ◽  
pp. no-no
Author(s):  
Boyoung Y. Park ◽  
Khoa D. Nguyen ◽  
Mani Raj Chaulagain ◽  
Venukrishnan Komanduri ◽  
Michael J. Krische
Keyword(s):  
Oxidative Addition ◽  
Primary Alcohols ◽  
Homoallylic Alcohols

scholarly journals Three-component coupling of aryl iodides, allenes, and aldehydes catalyzed by a Co/Cr-hybrid catalyst

2018 ◽  
Vol 14 ◽  
pp. 1413-1420 ◽  
Author(s):  
Kimihiro Komeyama ◽  
Shunsuke Sakiyama ◽  
Kento Iwashita ◽  
Itaru Osaka ◽  
Ken Takaki
Keyword(s):  
Reaction Mechanism ◽  
Cobalt Catalyst ◽  
Oxidative Addition ◽  
Hybrid Catalyst ◽  
Cobalt Chromium ◽  
Homoallylic Alcohols ◽  
Aryl Iodides ◽  
Chromium Salt ◽  
Three Component Coupling

The cobalt/chromium-catalyzed three-component coupling of aryl iodides, allenes, and aldehydes has been developed to afford multi-substituted homoallylic alcohols in a diastereoselective manner. Control experiments for understanding the reaction mechanism reveal that the cobalt catalyst is involved in the oxidative addition and carbometalation steps in the reaction, whereas the chromium salt generates highly nucleophilic allylchromium intermediates from allylcobalt species, without the loss of stereochemical information, to allow the addition to aldehydes.

Iridium-Catalyzed Coupling Reaction of Primary Alcohols with 1-Aryl-1-propynes Leading to Secondary Homoallylic Alcohols

2009 ◽  
Vol 11 (15) ◽  
pp. 3510-3513 ◽  
Author(s):  
Yasushi Obora ◽  
Shintaro Hatanaka ◽  
Yasutaka Ishii
Keyword(s):  
Coupling Reaction ◽  
Primary Alcohols ◽  
Homoallylic Alcohols

Some Problems in the Oxidative Addition and Binding of an Ethylene to a Transition Metal Center.

1987 ◽  
Vol 6 (4) ◽  
pp. 902-902
Author(s):  
Jerome Silestre ◽  
Maria Calhorda ◽  
Roald Hoffman ◽  
Page Stoutland ◽  
Robert Bergman
Keyword(s):  
Transition Metal ◽  
Oxidative Addition ◽  
Metal Center

Reversible Oxidative-Addition and Reductive-Elimination of Thiophene from a Titanium Complex and Its Thermally-Induced Hydrodesulfurization Chemistry

2019 ◽  
Author(s):  
Alejandra Gomez-Torres ◽  
J. Rolando Aguilar-Calderón ◽  
Carlos Saucedo ◽  
Aldo Jordan ◽  
Alejandro J. Metta-Magaña ◽  
...  
Keyword(s):  
Dft Calculations ◽  
Ring Opening ◽  
Thiophene Ring ◽  
Oxidative Addition ◽  
Reductive Elimination ◽  
Thermally Induced ◽  
Titanium Complex

<p>The masked Ti(II) synthon (<sup>Ket</sup>guan)(<i>η</i><sup>6</sup>-Im<sup>Dipp</sup>N)Ti (<b>1</b>) oxidatively adds across thiophene to give ring-opened (<sup>Ket</sup>guan)(Im<sup>Dipp</sup>N)Ti[<i>κ</i><sup>2</sup>-<i>S</i>(CH)<sub>3</sub><i>C</i>H] (<b>2</b>). Complex <b>2</b> is photosensitive, and upon exposure to light, reductively eliminates thiophene to regenerate <b>1</b> – a rare example of early-metal mediated oxidative-addition/reductive-elimination chemistry. DFT calculations indicate strong titanium π-backdonation to the thiophene π*-orbitals leads to the observed thiophene ring opening across titanium, while a proposed photoinduced LMCT promotes the reverse thiophene elimination from <b>2</b>. Finally, pressurizing solutions of <b>2 </b>with H<sub>2</sub> (150 psi) at 80 °C leads to the hydrodesulfurization of thiophene to give the Ti(IV) sulfide (<sup>Ket</sup>guan)(Im<sup>Dipp</sup>N)Ti(S) (<b>3</b>) and butane. </p>

Ni(0)-Catalyzed α-Allylic Alkylation of Regular Ketones with 1,3-Dienes under pH and Redox-neutral Conditions

2019 ◽  
Author(s):  
Tiantian Chen ◽  
Yang Yang ◽  
Liyu Xie ◽  
Haijian Yang ◽  
Guangbin Dong ◽  
...  
Keyword(s):  
Oxidative Addition ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Dual Role ◽  
Allylic Alkylation ◽  
Cross Coupling Reaction ◽  
Neutral Conditions

<p>We report a Ni(0)-catalyzed cross coupling reaction between simple ketones and 1,3-dienes. A variety of a-allylic alkylation products were formed in an 1,2-addition manner with excellent regioselectivity. Water was found to significantly accelerate this transformation. A HO-Ni-H species generated from oxidative addition of Ni(0) to H<sub>2</sub>O is proposed to play a “dual role” in activating both the ketone and the diene substrate.</p>

On the Reactivity of mRNA Caps: C-H Oxidative Addition of 7-Methylguanosine to Pt(0)

2019 ◽  
Author(s):  
Maria Ines Leitao ◽  
Carmen Gonzalez ◽  
Zuzanna Filipiak ◽  
Ana Petronilho
Keyword(s):  
Oxidative Addition ◽  
Carbene Complex ◽  
Proton Loss

<p>7-methylguanosine, the so-called mRNA cap 0 bears a very labile C8-H bond, due to the formation of an ylide/N-heterocyclic carbene, upon proton loss. The reaction of 7-methylguanosine with Pt(PPh3)4, via C-H oxidative addition, yields a hydrido–PtII carbene complex and this reactivity can be extrapolated to 7,9-dimethylguanine. </p>

Synthesis of Functionalized Homoallylic Alcohols Using Potassium Allyltrifluoroborate Promoted by Microwave Irradiation

2015 ◽  
Vol 2 (4) ◽  
pp. 403-408 ◽  
Author(s):  
Gilson B. da Silva ◽  
Jucleiton J. R. de Freitas ◽  
Paulo H. Menezes ◽  
Ivani Malvestiti
Keyword(s):  
Microwave Irradiation ◽  
Homoallylic Alcohols
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