t-BuOK-mediated reductive addition of P(O)–H compounds to terminal alkynes forming β-arylphosphine oxides

2017 ◽  
Vol 15 (26) ◽  
pp. 5462-5467 ◽  
Author(s):  
Ji-Shu Zhang ◽  
Jian-Qiu Zhang ◽  
Tieqiao Chen ◽  
Li-Biao Han
Keyword(s):  
Transfer Hydrogenation ◽  
Terminal Alkynes ◽  
Tandem Process ◽  
Selective Addition

A novel and efficient t-BuOK-mediated reductive addition of P(O)–H compounds to terminal alkynes forming β-arylphosphine oxides was developed. This reaction may proceed via a tandem process involving regio-selective addition and subsequent transfer hydrogenation.

scholarly journals Bis-NHC–Ag/Pd(OAc)2 Catalytic System Catalyzed Transfer Hydrogenation Reaction

Catalysts ◽  
2020 ◽  
Vol 11 (1) ◽  
pp. 8
Author(s):  
Hui-Ju Chen ◽  
Chien-Cheng Chiu ◽  
Tsui Wang ◽  
Dong-Sheng Lee ◽  
Ta-Jung Lu
Keyword(s):  
Functional Groups ◽  
Catalytic System ◽  
High Efficiency ◽  
Aqueous Media ◽  
Hydrogenation Reaction ◽  
Transfer Hydrogenation ◽  
Terminal Alkynes ◽  
Wide Range ◽  
Transfer Hydrogenation Reaction

The bis-NHC–Ag/Pd(OAc)2 catalytic system (NHC = N-heterocyclic carbene), a combination of bis-NHC–Ag complex and Pd(OAc)2, was found to be a smart catalyst in the Pd-catalyzed transfer hydrogenation of various functionalized arenes and internal/terminal alkynes. The catalytic system demonstrated high efficiency for the reduction of a wide range of various functional groups such as carbonyls, alkynes, olefins, and nitro groups in good to excellent yields and high chemoselectivity for the reduction of functional groups. In addition, the protocol was successfully exploited to stereoselectivity for the transformation of alkynes to alkenes in aqueous media under air. This methodology successfully provided an alternative useful protocol for reducing various functional groups and a simple operational protocol for transfer hydrogenation.

scholarly journals Ligand-Promoted Iridium-Catalyzed Transfer Hydrogenation of Terminal Alkynes with Ethanol and Its Application

ACS Omega ◽  
2019 ◽  
Vol 4 (14) ◽  
pp. 16045-16051 ◽  
Author(s):  
Chengniu Wang ◽  
Shengnan Gong ◽  
Zhipeng Liang ◽  
Yufeng Sun ◽  
Rui Cheng ◽  
...  
Keyword(s):  
Transfer Hydrogenation ◽  
Terminal Alkynes

scholarly journals Synthesis of Stereodefined 1,1-Diborylalkenes via Copper-Catalyzed Diboration of Terminal Alkynes

2020 ◽  
Author(s):  
Yang Gao ◽  
Zhong-Qian Wu ◽  
Keary Engle
Keyword(s):  
Functional Group ◽  
Aryl Halides ◽  
Terminal Alkynes ◽  
Mild Conditions ◽  
Tandem Process ◽  
Trisubstituted Alkenes

A copper-catalyzed method for the <i>E</i>-selective 1,1-diboration of terminal alkynes is described. The tandem process involves sequential dehydrogenative borylation of the alkyne substrate with HBdan (HBdan = 1,8-diaminonaphthalatoborane), followed by hydroboration with HBpin (HBpin = pinacolborane). This method proceeds efficiently under mild conditions, furnishing 1,1-diborylalkenes with excellent stereoselectivity and broad functional-group tolerance. Taking advantage of the different reactivities of the two boryl moieties, the products can then be employed in stepwise cross-couplings with aryl halides for the stereocontrolled construction of trisubstituted alkenes.

Synthesis of Medium-Sized Carbocycles by Gallium-Catalyzed Tandem Carbonyl-Olefin Metathesis/Transfer Hydrogenation

2019 ◽  
Author(s):  
Alexandre Djurovic ◽  
Marie Vayer ◽  
Zhilong Li ◽  
Régis Guillot ◽  
Jean Pierre Baltaze ◽  
...  
Keyword(s):  
Olefin Metathesis ◽  
Functional Group ◽  
Transfer Hydrogenation ◽  
Dft Computations ◽  
Tandem Process ◽  
Cyclic Alkenes

We report a catalytic tandem process involving a ring-closing carbonyl-olefin metathesis and a transfer hydrogenation. 1,4-Cyclohexadiene has been used as H<sub>2 </sub>surrogate to reduce the cyclic alkenes formed after the metathesis step. The same NHC-stabilized cationic gallium(III) complex, [IPr<b><sub>˙</sub></b>GaCl<sub>2</sub>][SbF<sub>6</sub>], performs the two steps with functional group tolerance. This reaction is stereoselective, leading either to 1,2-<i>cis</i>disubstituted cyclopentanes or to a variety of cyclohexanes. DFT computations support an unexpected mechanism involving the activation of 1,4-cyclohexadiene by superelectrophilic gallium(III) dimers.

Ruthenium-catalyzed redox isomerization/transfer hydrogenation in organic and aqueous media: A one-pot tandem process for the reduction of allylic alcohols

2009 ◽  
Vol 11 (12) ◽  
pp. 1992 ◽  
Author(s):  
Victorio Cadierno ◽  
Pascale Crochet ◽  
Javier Francos ◽  
Sergio E. García-Garrido ◽  
José Gimeno ◽  
...  
Keyword(s):  
Aqueous Media ◽  
Transfer Hydrogenation ◽  
Allylic Alcohols ◽  
One Pot ◽  
Tandem Process ◽  
Redox Isomerization

Ru-mediated selective addition reactions of carboxylic acids to internal and terminal alkynes

2010 ◽  
Vol 695 (19-20) ◽  
pp. 2161-2166 ◽  
Author(s):  
Solmaz Karabulut ◽  
Bengi Özgün Öztürk ◽  
Yavuz İmamoğlu
Keyword(s):  
Carboxylic Acids ◽  
Addition Reactions ◽  
Terminal Alkynes ◽  
Selective Addition

ChemInform Abstract: Asymmetric Transfer Hydrogenation of Ketones with Modified Grubbs′ Metathesis Catalysts: On the Way to a Tandem Process.

ChemInform ◽  
2016 ◽  
Vol 47 (27) ◽  
Author(s):  
Marc Renom-Carrasco ◽  
Piotr Gajewski ◽  
Luca Pignataro ◽  
Johannes G. de Vries ◽  
Umberto Piarulli ◽  
...  
Keyword(s):  
Transfer Hydrogenation ◽  
Asymmetric Transfer Hydrogenation ◽  
Tandem Process ◽  
Metathesis Catalysts ◽  
The Way

ChemInform Abstract: Ruthenium-Catalyzed Redox Isomerization/Transfer Hydrogenation in Organic and Aqueous Media: A One-Pot Tandem Process for the Reduction of Allylic Alcohols.

ChemInform ◽  
2010 ◽  
Vol 41 (18) ◽  
Author(s):  
Victorio Cadierno ◽  
Pascale Crochet ◽  
Javier Francos ◽  
Sergio E. Garcia-Garrido ◽  
Jose Gimeno ◽  
...  
Keyword(s):  
Aqueous Media ◽  
Transfer Hydrogenation ◽  
Allylic Alcohols ◽  
One Pot ◽  
Tandem Process ◽  
Redox Isomerization
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