Photoredox Mediated Asymmetric Cross-Dehydrogenative Coupling of Enones and Tertiary Amines by Chiral Primary Amine Catalysis

Synthesis ◽  
2021 ◽  
Author(s):  
Zongbin Jia ◽  
Qi Yang ◽  
Sanzhong Luo
Keyword(s):  
Primary Amine ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Tertiary Amines ◽  
Dehydrogenative Coupling ◽  
Cross Coupling Reaction ◽  
Iminium Ion ◽  
Amine Catalysis ◽  
Catalytic Asymmetric

We report herein a catalytic asymmetric dehydrogenative cross-coupling reaction between enones and tertiary amines enabled by synergistic photoredox and chiral primary amine catalysis. The reaction was proposed to proceed via the interception of iminium ion intermediate, in situ generated from photoredox oxidation, by dienamine at α-position, following by isomerization, leading to aza-Morita-Baylis-Hillman-type products with good diastereo- and enantio- selectivity.

scholarly journals Efficient in situ N-heterocyclic carbene palladium(ii) generated from Pd(OAc)2 catalysts for carbonylative Suzuki coupling reactions of arylboronic acids with 2-bromopyridine under inert conditions leading to unsymmetrical arylpyridine ketones: synthesis, characterization and cytotoxic activities

RSC Advances ◽  
2018 ◽  
Vol 8 (70) ◽  
pp. 40000-40015 ◽  
Author(s):  
Nedra Touj ◽  
Abdullah S. Al-Ayed ◽  
Mathieu Sauthier ◽  
Lamjed Mansour ◽  
Abdel Halim Harrath ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Suzuki Coupling ◽  
Boronic Acids ◽  
Cytotoxic Activities ◽  
Coupling Reactions ◽  
Component System ◽  
Arylboronic Acids ◽  
Cross Coupling Reaction

The in situ prepared four component system Pd(OAc)2, 1,3-dialkylbenzimidazolium halides 2a–i and 4a–i, K2CO3 under CO atmosphere catalyses carbonylative cross-coupling reaction of 2-bromopyridine with various boronic acids to yield unsymmetrical arylpyridine ketones.

scholarly journals A urea-modified tryptophan basedin situreducing and stabilizing agent for the fabrication of gold nanoparticles as a Suzuki–Miyaura cross-coupling catalyst in water

2019 ◽  
Vol 1 (4) ◽  
pp. 1380-1386 ◽  
Author(s):  
Supriya Sasmal ◽  
Mintu Debnath ◽  
Sujay Kumar Nandi ◽  
Debasish Haldar
Keyword(s):  
Gold Nanoparticles ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Stabilizing Agent ◽  
Cross Coupling Reaction ◽  
Reaction In Water

Urea modified tryptophan has been used as anin situreducing and stabilizing agent for the fabrication of gold nanoparticles and the gold nanoparticles efficiently catalyzed the Suzuki–Miyaura cross-coupling reaction in water.

Analysis of the water extract of waste papaya bark ash and its implications as an in situ base in the ligand-free recyclable Suzuki–Miyaura coupling reaction

RSC Advances ◽  
2016 ◽  
Vol 6 (34) ◽  
pp. 28981-28985 ◽  
Author(s):  
Manashi Sarmah ◽  
Anindita Dewan ◽  
Manoj Mondal ◽  
Ashim J. Thakur ◽  
Utpal Bora
Keyword(s):  
Room Temperature ◽  
Water Extract ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Basic Medium ◽  
Low Temperature Combustion ◽  
Cross Coupling Reaction ◽  
Ligand Free ◽  
Temperature Combustion

The conversion of waste papaya-bark to ash–water extract via low-temperature combustion, and its utilization as an efficient and eco-friendly in situ basic medium for Suzuki–Miyaura cross-coupling reaction at room temperature are reported.

Pd–NPs@MMT–K10 Catalysis of Suzuki–Miyaura Cross-coupling Reaction: In Situ Generation and Ex Situ Use

2021 ◽  
Author(s):  
Pubanita Bhuyan ◽  
Amar Jyoti Bhuyan ◽  
Palash Jyoti Gogoi ◽  
Abhijit Mahanta ◽  
Chandan Tamuly ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Ex Situ ◽  
Cross Coupling Reaction ◽  
In Situ Generation

A facile and convenient sequential homobimetallic catalytic approach towards β-methylstyrenes. A one-pot Stille cross-coupling/isomerization strategy

2014 ◽  
Vol 12 (22) ◽  
pp. 3735-3743 ◽  
Author(s):  
Sebastián O. Simonetti ◽  
Enrique L. Larghi ◽  
Teodoro S. Kaufman
Keyword(s):  
Double Bond ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Aryl Halides ◽  
One Pot ◽  
Cross Coupling Reaction

A one-pot approach towards β-methylstyrenes is reported. The transformation involves a Stille cross-coupling reaction of aryl halides with allyltributylstannane, followed by an in situ Pd-catalyzed double bond conjugative migration.

Ligand Free Heterogeneous Sonogashira Cross-Coupling Reaction over an in Situ Organoiodine Capsulized Palladium Anchored to a Perovskite Catalyst

2019 ◽  
Vol 7 (15) ◽  
pp. 12697-12706 ◽  
Author(s):  
Saba Alapour ◽  
Majid D. Farahani ◽  
Deresh Ramjugernath ◽  
Neil A. Koorbanally ◽  
Holger B. Friedrich
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Perovskite Catalyst ◽  
Cross Coupling Reaction ◽  
Ligand Free
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