Palladium-catalyzed Ugi-type reaction of 2-iodoanilines with isocyanides and carboxylic acids affording N-acyl anthranilamides

2021 ◽  
Author(s):  
Tuanli Yao ◽  
Bo Wang ◽  
Beige Ren ◽  
Qin Xiang Yang ◽  
Tao Li
Keyword(s):  
Carboxylic Acids ◽  
Multicomponent Reaction ◽  
Type Reaction ◽  
Highly Efficient ◽  
Efficient Access ◽  
Palladium Catalyzed

The first palladium-catalyzed Ugi-type multicomponent reaction for the synthesis of N-acyl anthranilamides from isocyanides, 2-iodoanilines and carboxylic acids has been developed. This method provides an expeditious and highly efficient access...

Palladium-Catalyzed Multicomponent Reaction of Alkynes, Carboxylic Acids, and Isocyanides: A Direct Approach to Captodative Olefins

2019 ◽  
Vol 21 (6) ◽  
pp. 1593-1597 ◽  
Author(s):  
Mingchun Gao ◽  
Minfen Zou ◽  
Jue Wang ◽  
Qitao Tan ◽  
Bingxin Liu ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Multicomponent Reaction ◽  
Direct Approach ◽  
Palladium Catalyzed

Intramolecular cross dehydrogenative coupling of 4-substituted coumarins: rapid and efficient access to coumestans and indole[3,2-c]coumarins

2016 ◽  
Vol 3 (9) ◽  
pp. 1111-1115 ◽  
Author(s):  
Chao Cheng ◽  
Wen-Wen Chen ◽  
Bin Xu ◽  
Ming-Hua Xu
Keyword(s):  
Highly Efficient ◽  
Dehydrogenative Coupling ◽  
Efficient Access ◽  
Palladium Catalyzed ◽  
Substituted Coumarins

A palladium-catalyzed highly efficient and atom-economical intramolecular cross dehydrogenative coupling (CDC) reaction to access fused polyheterocycles containing a coumarin nucleus has been developed.

A palladium/Et3N·HI-catalyzed highly selective 7-endo alkyl-Heck-type reaction of epoxides and a DFT study on the mechanism

2021 ◽  
Author(s):  
Xu Dong ◽  
Li-Ping Xu ◽  
Yi Yang ◽  
Yunxia Liu ◽  
Xin Li ◽  
...  
Keyword(s):  
Heck Reaction ◽  
Ring Opening ◽  
Dft Study ◽  
Type Reaction ◽  
Highly Efficient ◽  
Palladium Catalyzed ◽  
Ring Opening Of Epoxides

A highly efficient 7-endo alkyl-Heck reaction was achieved via palladium catalyzed ring-opening of epoxides, providing a variety of 6-aryl-2,3,4,7-tetrahydro-1H-azepin-3-ols and 6-aryl-2,3,4,5-tetrahydrooxepin-3-ols.

Ligand-Enabled γ-C(sp3)–H Olefination of Free Carboxylic Acids

2020 ◽  
Author(s):  
Kiron Kumar Ghosh ◽  
Alexander Uttry ◽  
Francesca Ghiringhelli ◽  
Arup Mondal ◽  
Manuel van Gemmeren
Keyword(s):  
Reaction Mechanism ◽  
Carboxylic Acids ◽  
Michael Addition ◽  
Kinetic Studies ◽  
Wide Range ◽  
Palladium Catalyzed

We report the ligand enabled C(sp3)–H activation/olefination of free carboxylic acids in the γ-position. Through an intramolecular Michael-addition, δ-lactones are obtained as products. Two distinct ligand classes are identified that enable the challenging palladium-catalyzed activation of free carboxylic acids in the γ-position. The developed protocol features a wide range of acid substrates and olefin reaction partners and is shown to be applicable on a preparatively useful scale. Insights into the underlying reaction mechanism obtained through kinetic studies are reported.<br>

Sequential C-Selective Difluoromethylation/Pd-Catalyzed Decarboxylative Protonation: An Efficient Access to Tertiary Difluoromethylated Scaffolds

2019 ◽  
Author(s):  
Nicolas Duchemin ◽  
Roberto Buccafusca ◽  
Marc Daumas ◽  
Vincent Ferey ◽  
Stellios Arseniyadis
Keyword(s):  
Drug Development ◽  
Late Stage ◽  
Efficient Access ◽  
Palladium Catalyzed ◽  
General Method

We report here a general method that allows a highly straightforward access to tertiary difluoromethylated compounds. The strategy relies on a two-step sequence featuring a C-selective electrophilic difluoromethylation and an unprecedented palladium-catalyzed decarboxylative protonation. Considering the generality of the method and the attractive properties offered by the difluoromethyl group, this approach provides a valuable tool for late-stage functionalization and drug development.<br>

Highly Efficient Four-Component Synthesis of 4(3H)-Quinazolinones: Palladium-Catalyzed Carbonylative Coupling Reactions

2013 ◽  
Vol 53 (5) ◽  
pp. 1420-1424 ◽  
Author(s):  
Lin He ◽  
Haoquan Li ◽  
Helfried Neumann ◽  
Matthias Beller ◽  
Xiao-Feng Wu
Keyword(s):  
Coupling Reactions ◽  
Highly Efficient ◽  
Palladium Catalyzed

Recent Developments in Heck-Type Reaction of Unactivated Alkenes and Alkyl Electrophiles

Synthesis ◽  
2020 ◽  
Author(s):  
Lili Shi ◽  
Junkai Fu ◽  
Shuangqiu Gao ◽  
Le Chang ◽  
Binglin Wang
Keyword(s):  
Heck Reaction ◽  
Alkyl Radicals ◽  
Type Reaction ◽  
The Past ◽  
Alkyl Electrophiles ◽  
Recent Developments ◽  
Palladium Catalyzed ◽  
Initial Work ◽  
Activated Olefins ◽  
Pseudo Halides

AbstractThe Mizoroki–Heck reaction is considered as one of the most ingenious and widely used methods for constructing C–C bonds. This reaction mainly focuses on activated olefins (styrenes, acrylates, or vinyl ethers) and aryl/vinyl (pseudo) halides. In comparison, the studies on unactivated alkenes and alkyl electrophiles are far less due to the low reactivity, poor selectivity, as well as competitive β-H elimination. In the past years, a growing interest has thus been devoted and significant breakthroughs have been achieved in the employment of unactivated alkenes and alkyl electrophiles as the reaction components, and this type of coupling is called as Heck-type or Heck-like reaction, which distinguishes from the traditional Heck reaction. Herein, we give a brief summary on Heck-type reaction between unactivated alkenes and alkyl electrophlies, covering its initial work, recent advancements, and mechanistic discussions.1 Introduction2 Intramolecular Heck-Type Reaction of Unactivated Alkenes and Alkyl Electrophiles2.1 Cobalt-Catalyzed Intramolecular Heck-Type Reaction2.2 Palladium-Catalyzed Intramolecular Heck-Type Reaction2.3 Nickel-Catalyzed Intramolecular Heck-Type Reaction2.4 Photocatalysis and Multimetallic Protocol for Intramolecular Heck-Type Reaction3 Intermolecular Heck-Type Reaction of Unactivated Alkenes and Alkyl Electrophiles3.1 Electrophilic Trifluoromethylating Reagent as Reaction Partners3.2 Alkyl Electrophiles as Reaction Partners4 Oxidative Heck-Type Reaction of Unactivated Alkenes and Alkyl Radicals5 Conclusions and Outlook

Sign in / Sign up

Export Citation Format

Share Document