scholarly journals Reactions of diborenes with terminal alkynes: mechanisms of ligand-controlled anti-selective hydroalkynylation, cycloaddition and C≡C triple bond scission

2021 ◽  
Author(s):  
Lukas Englert ◽  
Holger Braunschweig ◽  
Torsten Thiess ◽  
Fabian Schorr ◽  
Krzysztof Radacki ◽  
...  
Keyword(s):  
Triple Bond ◽  
Lewis Base ◽  
Terminal Alkynes ◽  
Bond Scission ◽  
Terminal Acetylenes

The reactions of terminal acetylenes with doubly Lewis base-stabilised diborenes resulted in different outcomes depending on the nature of the ligands at boron and the conformation of the diborene (cyclic...

Controllable assembly of the benzothiazole framework using a CC triple bond as a one-carbon synthon

2018 ◽  
Vol 54 (14) ◽  
pp. 1742-1745 ◽  
Author(s):  
Yubing Huang ◽  
Donghao Yan ◽  
Xu Wang ◽  
Peiqi Zhou ◽  
Wanqing Wu ◽  
...  
Keyword(s):  
Triple Bond ◽  
Elemental Sulfur ◽  
Terminal Alkynes ◽  
One Pot ◽  
Benzothiazole Derivatives

A one-pot protocol to controllably assemble diverse benzothiazole derivatives from o-haloanilines, elemental sulfur and terminal alkynes has been realized.

scholarly journals Phenylboronic Acid/CuSO4 as an Efficient Catalyst for the Synthesis of 1,4-Disubstituted-1,2,3-Triazoles from Terminal Acetylenes and Alkyl Azides

2017 ◽  
Vol 59 (2) ◽  
Author(s):  
Heraclio López-Ruiz
Keyword(s):  
Microwave Heating ◽  
Room Temperature ◽  
Phenylboronic Acid ◽  
Terminal Alkynes ◽  
Efficient Catalyst ◽  
Alkyl Azides ◽  
Terminal Acetylenes

<p>The synthesis of 1,4-disubstituted-1,2,3-triazoles from alkyl azides and terminal alkynes at room temperature and under microwave heating was attained using Cu(I), generated <em>in-situ </em>from copper(II) sulfate and phenylboronic acid, as catalyst. Twelve new triazoles were obtained in moderate to good yields (53-98%), and the products were obtained by crystallization from the mixture reaction without further purification.</p>

Palladium-catalyzed aerobic oxidative cross-coupling of arylhydrazines with terminal alkynes

2015 ◽  
Vol 51 (68) ◽  
pp. 13272-13274 ◽  
Author(s):  
Yingwei Zhao ◽  
Qiuling Song
Keyword(s):  
Oxidative Coupling ◽  
Cross Coupling ◽  
Terminal Alkynes ◽  
Palladium Catalyzed ◽  
Terminal Acetylenes

The Pd-catalyzed aerobic oxidative coupling of arylhydrazines with terminal acetylenes was achieved under copper- and base-free conditions.

Copper(i)-catalysed oxidative C–N coupling of 2-aminopyridine with terminal alkynes featuring a CC bond cleavage promoted by visible light

2016 ◽  
Vol 52 (79) ◽  
pp. 11756-11759 ◽  
Author(s):  
Ayyakkannu Ragupathi ◽  
Arunachalam Sagadevan ◽  
Chun-Cheng Lin ◽  
Jih-Ru Hwu ◽  
Kuo Chu Hwang
Keyword(s):  
Visible Light ◽  
Triple Bond ◽  
Room Temperature ◽  
Bond Cleavage ◽  
Terminal Alkynes

An efficient and eco-friendly approach to aerobic oxidative C–N coupling of 2-aminopyridine with terminal alkynes for preparation of biologically important pyridyl-amides via CC triple bond cleavage at room temperature.

A useful method for preparation of carboxylic acids from terminal alkynes

1983 ◽  
Vol 61 (10) ◽  
pp. 2423-2424 ◽  
Author(s):  
Suzanne R. Abrams
Keyword(s):  
Acetic Acid ◽  
Sulfuric Acid ◽  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Chain Length ◽  
Good Yield ◽  
Terminal Alkynes ◽  
Terminal Acetylenes ◽  
Long Chain ◽  
Acetic Acids

Substituted acetic acids can be prepared in good yield (50–80%) from terminal acetylenes of the same chain length. The alkyne is first converted to the thiophenyl ether, which is treated without purification with mercuric sulfate in acetic acid and 2 N sulfuric acid affording the carboxylic acid. The method is particularly useful in the synthesis of long chain ω-hydroxyalkanoic acids.

General and selective syn-carboxylation-trifluoromethylation of terminal alkynes: application to the late-stage modification of dehydrocholic acid

2019 ◽  
Vol 55 (28) ◽  
pp. 4099-4102 ◽  
Author(s):  
Song-Lin Zhang ◽  
Chang Xiao ◽  
Hai-Xing Wan ◽  
Xiaoming Zhang
Keyword(s):  
Late Stage ◽  
Triple Bond ◽  
Biologically Active ◽  
Terminal Alkynes ◽  
Dehydrocholic Acid ◽  
Enol Esters

A general and selective syn-carboxylation-trifluoromethylation across the triple bond of terminal alkynes is developed by virtue of a reactive Cu(iii)–CF3 complex, which produces a broad range of biologically active trifluoromethylated enol esters with excellent regio- and stereoselectivity.

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.

scholarly journals The effects of amines on oxidative homo-coupling of terminal alkynes promoted by copper salts

2005 ◽  
Vol 2005 (2) ◽  
pp. 112-115 ◽  
Author(s):  
Lei Wang ◽  
Jincan Yan ◽  
Pinhua Li ◽  
Min Wang ◽  
Caina Su
Keyword(s):  
Reaction Medium ◽  
Cross Coupling ◽  
Catalytic Amount ◽  
Sonogashira Reaction ◽  
Coupling Reactions ◽  
Sonogashira Coupling ◽  
Terminal Alkynes ◽  
Copper Salts ◽  
Terminal Acetylenes ◽  
Glaser Coupling

The effects of all kinds of amines on homo-couplings (Glaser reactions) of terminal alkynes promoted by copper salts and the Sonogashira coupling reactions were studied systematically. Diethylamine (2° amine) can serve as an excellent solvent, base and coordination ligand in the oxidative homo-coupling of terminal alkynes and several modified Glaser coupling procedures have been developed which are based on a catalytic amount of cuprous salts (CuI, CuBr or CuCl) with diethylamine systems. Homo-coupling of terminal acetylenes in the Sonogashira reaction could be inhibited by using triethylamine (3° amine) as reaction medium, and the cross-coupling products were formed as the exclusive products.

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