Competitive Copper Catalysis in the Condensation of Primary Nitro Compounds with Terminal Alkynes: Synthesis of Isoxazoles

2016 ◽  
Vol 2016 (27) ◽  
pp. 4643-4655 ◽  
Author(s):  
Ausilia Baglieri ◽  
Luca Meschisi ◽  
Francesco De Sarlo ◽  
Fabrizio Machetti
Keyword(s):  
Nitro Compounds ◽  
Copper Catalysis ◽  
Terminal Alkynes

scholarly journals Copper-catalyzed α-selective hydrostannylation of alkynes for the synthesis of branched alkenylstannanes

2015 ◽  
Vol 51 (53) ◽  
pp. 10616-10619 ◽  
Author(s):  
H. Yoshida ◽  
A. Shinke ◽  
Y. Kawano ◽  
K. Takaki
Keyword(s):  
Copper Catalysis ◽  
Terminal Alkynes ◽  
Universal System

A universal system for highly α-selective hydrostannylation of terminal alkynes has been developed by use of a distannane or a silylstannane as a stannylating reagent under copper catalysis.

scholarly journals Borylstannylation of alkynes with inverse regioselectivity: copper-catalyzed three-component coupling using a masked diboron

2015 ◽  
Vol 51 (29) ◽  
pp. 6297-6300 ◽  
Author(s):  
H. Yoshida ◽  
Y. Takemoto ◽  
K. Takaki
Keyword(s):  
Triple Bond ◽  
Copper Catalysis ◽  
Terminal Alkynes ◽  
Straightforward Manner ◽  
Three Component Coupling

Masked boryl and stannyl moieties are smoothly installed into a carbon–carbon triple bond of diverse terminal alkynes under copper catalysis to provide cis-boryl(stannyl)alkenes in a straightforward manner. The regioselectivity is totally inverted to those of the previous borylstannylations, where a masked boryl moiety is attached to an internal carbon of alkynes.

Relay Palladium/Copper Catalysis Enabled Silylative [5 + 1] Benzannulation Using Terminal Alkynes as One-Carbon Units

2020 ◽  
Vol 22 (21) ◽  
pp. 8544-8549 ◽  
Author(s):  
Li-Jun Wu ◽  
Fan Teng ◽  
Gui-Fen Lv ◽  
Jin-Heng Li
Keyword(s):  
Copper Catalysis ◽  
Terminal Alkynes

scholarly journals Origins of Internal Regioselectivity in Copper-Catalyzed Borylation of Terminal Alkynes

2021 ◽  
Author(s):  
Takumi Tsushima ◽  
Hideya Tanaka ◽  
Kazuki Nakanishi ◽  
Masaaki Nakamoto ◽  
Hiroto Yoshida
Keyword(s):  
Chemical Synthesis ◽  
Cross Coupling ◽  
Lewis Acidity ◽  
Copper Catalysis ◽  
Terminal Alkynes ◽  
Challenging Issue ◽  
Universal Approach ◽  
Copper Center

<p>Installation of a boron functionality into a more substituted carbon of terminal alkynes has been a challenging issue in chemical synthesis, since inherently Lewis acidic boron moieties, in principle, favor their attachment to a terminal carbon. Herein, we report on the highly internal-selective borylation of terminal alkynes under copper catalysis, wherein diminishment of boron-Lewis acidity and ligand-derived steric bulk around a copper center are the key to the success. In particular, the use of an anthranilamide-substituted boron moiety [B(aam)] is of high synthetic significance, because its properly diminished Lewis acidity enabled the internal regioselectivity and the Suzuki–Miyaura cross-coupling activity to be compatibly achieved. This method provided direct and universal approach to variously substituted branched alkenylboron compounds, regardless of electronic and steric properties of a substituent on terminal alkynes.</p>

scholarly journals Origins of Internal Regioselectivity in Copper-Catalyzed Borylation of Terminal Alkynes

2021 ◽  
Author(s):  
Takumi Tsushima ◽  
Hideya Tanaka ◽  
Kazuki Nakanishi ◽  
Masaaki Nakamoto ◽  
Hiroto Yoshida
Keyword(s):  
Chemical Synthesis ◽  
Cross Coupling ◽  
Lewis Acidity ◽  
Copper Catalysis ◽  
Terminal Alkynes ◽  
Challenging Issue ◽  
Universal Approach ◽  
Copper Center

<p>Installation of a boron functionality into a more substituted carbon of terminal alkynes has been a challenging issue in chemical synthesis, since inherently Lewis acidic boron moieties, in principle, favor their attachment to a terminal carbon. Herein, we report on the highly internal-selective borylation of terminal alkynes under copper catalysis, wherein diminishment of boron-Lewis acidity and ligand-derived steric bulk around a copper center are the key to the success. In particular, the use of an anthranilamide-substituted boron moiety [B(aam)] is of high synthetic significance, because its properly diminished Lewis acidity enabled the internal regioselectivity and the Suzuki–Miyaura cross-coupling activity to be compatibly achieved. This method provided direct and universal approach to variously substituted branched alkenylboron compounds, regardless of electronic and steric properties of a substituent on terminal alkynes.</p>

Copper Catalysis for Selective Heterocoupling of Terminal Alkynes

2016 ◽  
Vol 138 (38) ◽  
pp. 12348-12351 ◽  
Author(s):  
Lebin Su ◽  
Jianyu Dong ◽  
Long Liu ◽  
Mengli Sun ◽  
Renhua Qiu ◽  
...  
Keyword(s):  
Copper Catalysis ◽  
Terminal Alkynes

Copper-Catalyzed Hydrocarboxylation of Allenes

2019 ◽  
Author(s):  
Rémi blieck ◽  
Marc Taillefer ◽  
Florian Monnier
Keyword(s):  
Carboxylic Acids ◽  
Copper Catalysis ◽  
Ligand Free ◽  
First Time

The addition of carboxylic acids to allenes was performed for the first time with copper catalysis. The hydrocarboxylation reaction is totally regio- and stereoselective, ligand-free and used catalytic amounts of copper and base.

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