A Bifunctional Ligand Enables Gold-Catalyzed Hydroarylation of Terminal Alkynes under Soft Reaction Conditions

2020 ◽  
Vol 22 (15) ◽  
pp. 6045-6049 ◽  
Author(s):  
Ting Li ◽  
Yuhan Yang ◽  
Baomin Luo ◽  
Bo Li ◽  
Luyi Zong ◽  
...  
Keyword(s):  
Terminal Alkynes ◽  
Reaction Conditions ◽  
Bifunctional Ligand

Catalytic asymmetric addition reactions leading to carbon-carbon bond formation: Phenyl and alkenyl transfer to aldehydes and alkynylation of α-imino esters

2006 ◽  
Vol 78 (2) ◽  
pp. 267-274 ◽  
Author(s):  
Jian-Xin Ji ◽  
Jing Wu ◽  
Lijin Xu ◽  
Chiu-Wing Yip ◽  
Kim Hung Lam ◽  
...  
Keyword(s):  
Bond Formation ◽  
Optically Active ◽  
Amino Acid Derivatives ◽  
Addition Reactions ◽  
Terminal Alkynes ◽  
Reaction Conditions ◽  
Carbon Carbon Bond ◽  
Catalytic Asymmetric ◽  
High Yields ◽  
Imino Esters

Optically active tertiary aminonaphthol ligands were obtained by a new, convenient procedure and were found to catalyze the enantioselective alkenyl and phenyl transfer to aldehydes in high yields and excellent enantiomeric excesses (ee's). The catalytic asymmetric introduction of alkynyl functionality to α-amino acid derivatives was realized by the direct addition of terminal alkynes to α-imino ester in the presence of chiral copper(I) complex under mild reaction conditions.

scholarly journals Synthesis of Alkynyl Ketones by Sonogashira Cross-Coupling of Acyl Chlorides with Terminal Alkynes Mediated by Palladium Catalysts Deposited over Donor-Functionalized Silica Gel

Catalysts ◽  
2020 ◽  
Vol 10 (10) ◽  
pp. 1186
Author(s):  
Miloslav Semler ◽  
Filip Horký ◽  
Petr Štěpnička
Keyword(s):  
Silica Gel ◽  
Palladium Catalysts ◽  
Cross Coupling ◽  
Significant Loss ◽  
Terminal Alkynes ◽  
Reaction Conditions ◽  
Co Catalyst ◽  
Acyl Chlorides ◽  
Good Catalytic Activity ◽  
Repeated Use

Palladium catalysts deposited over silica gel bearing simple amine (≡Si(CH2)3NH2) and composite functional amide pendants equipped with various donor groups in the terminal position (≡Si(CH2)3NHC(O)CH2Y, Y = SMe, NMe2 and PPh2) were prepared and evaluated in Sonogashira-type cross-coupling of acyl chlorides with terminal alkynes to give 1,3-disubstituted prop-2-yn-1-ones. Generally, the catalysts showed good catalytic activity in the reactions of aroyl chlorides with aryl alkynes under relatively mild reaction conditions even without adding a copper co-catalyst. However, their repeated use was compromised by a significant loss of activity after the first catalytic run.

Synthesis of 6-Alkynyl-6-hydroxyindoloquinazolinone Scaffolds via Copper-Catalyzed Alkynylation of Tryptanthrins

Synlett ◽  
2021 ◽  
Author(s):  
Yu Guo ◽  
Ebrahim-Alkhalil M. A. Ahmed ◽  
Hongxin Liu ◽  
Xinhua Li ◽  
Juan Li ◽  
...  
Keyword(s):  
Functional Group ◽  
Building Blocks ◽  
Sonogashira Coupling ◽  
Terminal Alkynes ◽  
Reaction Conditions

We report a copper catalyzed direct alkynylation reaction of tryptanthrins with terminal alkynes under mild reaction conditions. The developed method provides an array of synthetic building blocks of 6-alkynyl-6-hydroxyindoloquinazolinone compounds in moderate to good yields with varied functional group compatibility. Furthermore, the obtained adducts can be smoothly converted into versatile building blocks via hydrogenation, hydration and further Sonogashira coupling transformations.

scholarly journals Synthesis of α,β-unsaturated ketones through nickel-catalysed aldehyde-free hydroacylation of alkynes

2021 ◽  
Author(s):  
Joon Ho Rhlee ◽  
Saikat Maiti ◽  
Ho Seung Lee ◽  
Soochan Lee ◽  
Jaehyun Park ◽  
...  
Keyword(s):  
Transition Metal ◽  
Functional Groups ◽  
Room Temperature ◽  
Functional Materials ◽  
Ruthenium Catalysts ◽  
Terminal Alkynes ◽  
Acylating Agent ◽  
Reaction Conditions ◽  
Coupling Process ◽  
Unsaturated Ketones

Abstract α,β-Unsaturated ketones are common feedstocks in functional materials, pharmaceuticals and natural compounds. Transition metal-catalysed hydroacylation reactions of alkynes using aldehydes have been widely applied for the atom-economical synthesis of α,β-unsaturated ketones through chemoselective aldehydic C–H activation. However, previous hydroacylation reactions using rhodium, cobalt, or ruthenium catalysts require chelating moiety-bearing aldehydes to prevent undesired decarbonylative product via an unstable acyl-metal-H complex. Herein, we report a nickel-catalysed reductive and anti-Markovnikov selective coupling process to afford non-tethered E-enones from terminal alkynes through an acyl-nickel-thiopyridine complex in the presence of zinc metal as a reducing agent. Utilization of a thioester as an acylating agent and water as a hydrogen donor enables this mechanistically distinctive and aldehyde-free hydroacylation of terminal alkynes under mild reaction conditions at room temperature, with a broad substrate scope including versatile functional groups and even simple aryl and alkyl moieties.

Cobalt-catalyzed Glaser-type Homocoupling Reaction

Synthesis ◽  
2021 ◽  
Author(s):  
Keyin Ye ◽  
Jun-Fa Han ◽  
Peng Guo ◽  
Lin Chen
Keyword(s):  
Natural Products ◽  
Late Stage ◽  
Terminal Alkynes ◽  
Reaction Conditions ◽  
Highly Efficient ◽  
Homocoupling Reaction

A highly efficient cobalt-catalyzed homocoupling of terminal alkynes with di-tert-butyldiaziridinone as the oxidant has been developed. The protocol tolerates a wide array of terminal alkynes, both activated and unactivated alkynes, to afford their corresponding conjugated 1,3-diynes. The mild reaction conditions further allow late-stage homocoupling of alkynes derived from complex natural products.

A One-Pot Method for the Synthesis of Phenylalkynyl-Substituted Terminal Alkynes by Deprotection/Stannylation followed by a Migita–Kosugi–Stille coupling

2018 ◽  
Vol 42 (5) ◽  
pp. 235-238 ◽  
Author(s):  
Li-fen Peng ◽  
Bing-hao Wang ◽  
Ming Wang ◽  
Zi-long Tang ◽  
Yan-zi Jiang ◽  
...  
Keyword(s):  
Phosphine Oxide ◽  
Functional Group ◽  
Sonogashira Coupling ◽  
Terminal Alkynes ◽  
Synthetic Route ◽  
Stille Coupling ◽  
Reaction Conditions ◽  
One Pot

A practical one-pot approach for the synthesis of arylalkynyl-substituted terminal alkynes has been developed through a deprotection/ stannylation of a phenylethynyl phosphine oxide followed by Migita–Kosugi–Stille coupling, avoiding the longer synthetic route involving repeated deprotection/Sonogashira coupling. Other features of this approach include mild reaction conditions, excellent yields, facile isolation of products and wide functional group tolerance.

Chloramine Salt Mediated Oxidative Halogenation of Terminal Alkynes with KI or NaBr: Practical Synthesis of 1-Bromoalkynes and 1-Iodoalkynes

Synlett ◽  
2018 ◽  
Vol 29 (15) ◽  
pp. 2051-2055 ◽  
Author(s):  
Peijun Liu ◽  
Xiaozu Liu ◽  
Guojun Chen ◽  
Chenglong Li
Keyword(s):  
Terminal Alkynes ◽  
Reaction Conditions ◽  
Practical Synthesis ◽  
Oxidative Halogenation

A direct oxidative halogenation of terminal alkynes has been realized using chloramine-B as the oxidant and KI or NaBr as the halogen source. This reaction enables a general and practical access to synthetically valuable 1-bromoalkynes and 1-iodoalkynes in good to excellent yields under mild reaction conditions.

Sign in / Sign up

Export Citation Format

Share Document