scholarly journals Enantiocontrol by assembled attractive interactions in copper-catalyzed asymmetric direct alkynylation of α-ketoesters with terminal alkynes: OH⋯O/sp3-CH⋯O two-point hydrogen bonding combined with dispersive attractions

2018 ◽  
Vol 9 (14) ◽  
pp. 3484-3493 ◽  
Author(s):  
Martin C. Schwarzer ◽  
Akane Fujioka ◽  
Takaoki Ishii ◽  
Hirohisa Ohmiya ◽  
Seiji Mori ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Copper Catalyst ◽  
Terminal Alkynes

A chiral copper catalyst selects enantiofaces by assembled attractive interactions.

Efficient Carboxylation of Terminal Alkynes with Carbon Dioxide Catalyzed by Ligand‐Free Copper Catalyst under Ambient Conditions

2019 ◽  
Vol 8 (8) ◽  
pp. 1501-1505 ◽  
Author(s):  
Wan‐Hui Wang ◽  
Lihong Jia ◽  
Xiujuan Feng ◽  
Dingqiao Fang ◽  
Hongyu Guo ◽  
...  
Keyword(s):  
Carbon Dioxide ◽  
Copper Catalyst ◽  
Terminal Alkynes ◽  
Ambient Conditions ◽  
Ligand Free

scholarly journals One-Pot Synthesis of (Z)-β-Halovinyl Ketones via the Cascade of Sonogashira Coupling and Hydrohalogenation

2021 ◽  
Vol 8 ◽  
Author(s):  
Fa-Jie Chen ◽  
Zhenguo Hua ◽  
Jianhui Chen ◽  
Jiajia Chen ◽  
Daesung Lee ◽  
...  
Keyword(s):  
Efficient Method ◽  
Room Temperature ◽  
Copper Catalyst ◽  
High Yield ◽  
Sonogashira Coupling ◽  
Terminal Alkynes ◽  
Acid Chlorides ◽  
Triflic Acid ◽  
One Pot

Herein, we report an efficient method for the synthesis of (Z)-β-halovinyl ketones through a one-pot Sonogashira coupling and hydrohalogenation reaction promoted by palladium-copper catalyst and Brønsted acid. The ynone intermediates are generated in situ from readily available acid chlorides and terminal alkynes at room temperature, which are directly converted to (Z)-β-halovinyl ketones by treating with triflic acid. This method avoids the use of an external halogen source and features broad substrate scope, high yield, and good to excellent stereoselectivity.

scholarly journals Copper-catalyzed direct transformation of simple alkynes to alkenyl nitriles via aerobic oxidative N-incorporation

2015 ◽  
Vol 6 (11) ◽  
pp. 6355-6360 ◽  
Author(s):  
Xiaoqiang Huang ◽  
Xinyao Li ◽  
Ning Jiao
Keyword(s):  
Late Stage ◽  
Copper Catalyst ◽  
Terminal Alkynes ◽  
Direct Transformation ◽  
N Incorporation

A novel Cu-catalyzed aerobic oxidative N-incorporation into aliphatic terminal alkynes for the synthesis of alkenyl nitriles has been reported. The usage of inexpensive copper catalyst, O2as the sole oxidant, broad substrate scope as well as the feasibility for “the late-stage modification” make this protocol very promising.

Hydrogen-Bonding Controlled Nickel-Catalyzed Regioselective Cyclotrimerization of Terminal Alkynes

2021 ◽  
Author(s):  
Kai Yang ◽  
Pengfei Wang ◽  
Ze-Ying Sun ◽  
Minjie Guo ◽  
Wentao Zhao ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Terminal Alkynes

scholarly journals A Bifunctional Copper Catalyst Enables Ester Reduction with H2: Expanding the Reactivity Space of Nucleophilic Copper Hydrides

2021 ◽  
Author(s):  
Birte Zimmermann ◽  
Trung Tran Ngoc ◽  
Dimitrios-Ioannis Tzaras ◽  
Trinadh Kaicharla ◽  
Johannes F. Teichert
Keyword(s):  
Hydrogen Bonding ◽  
Copper Catalyst ◽  
Hydride Transfer ◽  
Bifunctional Catalyst ◽  
Reducing Agents ◽  
Reducing Agent ◽  
Reduction Step ◽  
First Time ◽  
The Way

Employing a bifunctional catalyst based on a copper(I)/NHC complex and a guanidine organocatalyst, catalytic ester reductions to alcohols with H<sub>2</sub> as terminal reducing agent are facilitated. The approach taken here enables the simul-taneous activation of esters through hydrogen bonding and formation of nucleophilic copper(I) hydrides from H<sub>2</sub>, resulting in a catalytic hydride transfer to esters. The reduction step is further facilitated by a proton shuttle mediated by the guani-dinium subunit. This bifunctional approach to ester reductions for the first time shifts the reactivity of generally considered “soft” copper(I) hydrides to previously unreactive “hard” ester electrophiles and paves the way for a replacement of stoichi-ometric reducing agents by a catalyst and H<sub>2</sub>.<br>

scholarly journals A Bifunctional Copper Catalyst Enables Ester Reduction with H2: Expanding the Reactivity Space of Nucleophilic Copper Hydrides

2021 ◽  
Author(s):  
Birte Zimmermann ◽  
Trung Tran Ngoc ◽  
Dimitrios-Ioannis Tzaras ◽  
Trinadh Kaicharla ◽  
Johannes F. Teichert
Keyword(s):  
Hydrogen Bonding ◽  
Copper Catalyst ◽  
Hydride Transfer ◽  
Bifunctional Catalyst ◽  
Reducing Agents ◽  
Reducing Agent ◽  
Reduction Step ◽  
First Time ◽  
The Way

Employing a bifunctional catalyst based on a copper(I)/NHC complex and a guanidine organocatalyst, catalytic ester reductions to alcohols with H<sub>2</sub> as terminal reducing agent are facilitated. The approach taken here enables the simul-taneous activation of esters through hydrogen bonding and formation of nucleophilic copper(I) hydrides from H<sub>2</sub>, resulting in a catalytic hydride transfer to esters. The reduction step is further facilitated by a proton shuttle mediated by the guani-dinium subunit. This bifunctional approach to ester reductions for the first time shifts the reactivity of generally considered “soft” copper(I) hydrides to previously unreactive “hard” ester electrophiles and paves the way for a replacement of stoichi-ometric reducing agents by a catalyst and H<sub>2</sub>.<br>

A facile access to N-sulfonylthioimidates and their use for the transformation to 3,4-dihydroquinazolines

2020 ◽  
Vol 18 (43) ◽  
pp. 8881-8885
Author(s):  
Jia-Yu Wu ◽  
Wei-Jr Liao ◽  
Xiu-Yi Lin ◽  
Chien-Fu Liang
Keyword(s):  
Copper Catalyst ◽  
Terminal Alkynes ◽  
Sulfonyl Azide

N-sulfonylthioimidates can be synthesized via terminal alkynes, sulfonyl azide, and thiols using a copper catalyst in the presence of 4-dimethylaminopyridine. Subsequently, it can be transformed to crucial pharmacophores of 3,4-dihydroquinazoline.

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