Computational and experimental studies on Cu/Au-catalyzed stereoselective synthesis of 1,3-disubstituted allenes

2019 ◽  
Vol 6 (11) ◽  
pp. 1780-1786 ◽  
Author(s):  
María Magdalena Cid ◽  
María Lago-Silva ◽  
Marta González Comesaña ◽  
Olalla Nieto Faza ◽  
Carlos Silva López
Keyword(s):  
Stereoselective Synthesis ◽  
Experimental Studies ◽  
Terminal Alkynes ◽  
Mechanistic Investigation

Thorough mechanistic investigation unveils details of the allenylation of terminal alkynes (ATA) under Crabbé-like conditions allowing for an enantioselective approach.

Theoretical and experimental studies of palladium-catalyzed site-selective C(sp3)−H bond functionalization enabled by transient ligands

2017 ◽  
Author(s):  
Haibo Ge ◽  
Lei Pan ◽  
Piaoping Tang ◽  
Ke Yang ◽  
Mian Wang ◽  
...  
Keyword(s):  
Bond Activation ◽  
Theoretical Calculations ◽  
Experimental Studies ◽  
Bond Functionalization ◽  
Aliphatic Ketones ◽  
Site Selectivity ◽  
Mechanistic Investigation ◽  
Palladium Catalyzed ◽  
Metal Catalyzed ◽  
Site Selective

Transition metal-catalyzed selective C–H bond functionalization enabled by transient ligands has become an extremely attractive topic due to its economical and greener characteristics. However, catalytic pathways of this reaction process on unactivated sp<sup>3</sup> carbons of reactants have not been well studied yet. Herein, detailed mechanistic investigation on Pd-catalyzed C(sp<sup>3</sup>)–H bond activation with amino acids as transient ligands has been systematically conducted. The theoretical calculations showed that higher angle distortion of C(sp2)-H bond over C(sp3)-H bond and stronger nucleophilicity of benzylic anion over its aromatic counterpart, leading to higher reactivity of corresponding C(sp<sup>3</sup>)–H bonds; the angle strain of the directing rings of key intermediates determines the site-selectivity of aliphatic ketone substrates; replacement of glycine with β-alanine as the transient ligand can decrease the angle tension of the directing rings. Synthetic experiments have confirmed that β-alanine is indeed a more efficient transient ligand for arylation of β-secondary carbons of linear aliphatic ketones than its glycine counterpart.<br><br>

Mechanistic Investigation of Rh(I)-Catalyzed Asymmetric Suzuki-Miyaura Coupling with Racemic Allyl Halides

2019 ◽  
Author(s):  
Lucy van Dijk ◽  
Ruchuta Ardkhean ◽  
Mireia Sidera ◽  
Sedef Karabiyikoglu ◽  
Özlem Sari ◽  
...  
Keyword(s):  
Quantum Chemical Calculations ◽  
Quantum Chemical ◽  
Experimental Studies ◽  
Mechanistic Investigation ◽  
Allyl Halides

A mechanism for Rh(I)-catalyzed asymmetric Suzuki-Miyaura coupling with racemic allyl halides is proposed based on a combination of experimental studies and quantum chemical calculations. <br>

scholarly journals Alkoxide-catalyzed addition of alkyl carbonates across alkynes – stereoselective synthesis of (E)-β-alkoxyacrylates

2017 ◽  
Vol 19 (3) ◽  
pp. 643-646
Author(s):  
Timo Wendling ◽  
Eugen Risto ◽  
Benjamin Erb ◽  
Lukas J. Gooßen
Keyword(s):  
Stereoselective Synthesis ◽  
Terminal Alkynes ◽  
Potassium Methoxide ◽  
Stereoselective Addition

Terminal alkynes were converted to (E)-β-alkoxyacrylates via regio- and stereoselective addition of dialky carbonates catalyzed by potassium methoxide.

scholarly journals Selective oxymetalation of terminal alkynes via 6-endo cyclization: mechanistic investigation and application to the efficient synthesis of 4-substituted isocoumarins

2018 ◽  
Vol 9 (28) ◽  
pp. 6041-6052 ◽  
Author(s):  
Yuji Kita ◽  
Tetsuji Yata ◽  
Yoshihiro Nishimoto ◽  
Kouji Chiba ◽  
Makoto Yasuda
Keyword(s):  
Terminal Alkynes ◽  
Efficient Synthesis ◽  
Mechanistic Investigation

The oxymetalation of terminal alkynes proceeded in a 6-endo cyclization manner with the use of indium or gallium trihalide.

Stereoselective Synthesis of (Z)-1,2-Diarylthio-1-alkene via the Reaction of Diaryl Disulfides with Terminal Alkynes Catalyzed by Cesium Hydroxide

2009 ◽  
Vol 39 (14) ◽  
pp. 2464-2471 ◽  
Author(s):  
Kang Bing Zou ◽  
Xian Hong Yin ◽  
Wen Qi Liu ◽  
Ren Hua Qiu ◽  
Ruo Xin Li ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Terminal Alkynes ◽  
Cesium Hydroxide

ChemInform Abstract: Stereoselective Synthesis of 2,3-Dihydropyrroles from Terminal Alkynes, Azides, and α,β-Unsaturated Aldehydes via N-Sulfonyl-1,2,3-triazoles.

ChemInform ◽  
2014 ◽  
Vol 45 (11) ◽  
pp. no-no
Author(s):  
Tomoya Miura ◽  
Takamasa Tanaka ◽  
Kentaro Hiraga ◽  
Scott G. Stewart ◽  
Masahiro Murakami
Keyword(s):  
Stereoselective Synthesis ◽  
Terminal Alkynes ◽  
Unsaturated Aldehydes
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