Palladium-Catalyzed Decarboxylative Aza-Michael Addition−Allylation Reactions between Allyl Carbamates and Activated Olefins. Generation of Quaternary Carbon Adjacent to Secondary Amine Carbon Center

2006 ◽  
Vol 71 (18) ◽  
pp. 6991-6995 ◽  
Author(s):  
Nitin T. Patil ◽  
Zhibao Huo ◽  
Yoshinori Yamamoto
Keyword(s):  
Secondary Amine ◽  
Michael Addition ◽  
Quaternary Carbon ◽  
Palladium Catalyzed ◽  
Activated Olefins

Michael Addition Catalyzed by Chiral Secondary Amine Phosphoramide Using Fluorinated Silyl Enol Ethers: Formation of Quaternary Carbon Stereocenters

2015 ◽  
Vol 127 (25) ◽  
pp. 7489-7493 ◽  
Author(s):  
Jin-Sheng Yu ◽  
Fu-Min Liao ◽  
Wei-Ming Gao ◽  
Kui Liao ◽  
Run-Lin Zuo ◽  
...  
Keyword(s):  
Secondary Amine ◽  
Michael Addition ◽  
Quaternary Carbon ◽  
Enol Ethers ◽  
Silyl Enol Ethers

Highly efficient synthesis of benzodioxins with a 2-site quaternary carbon structure by secondary amine-catalyzed dual Michael cascade reactions

2018 ◽  
Vol 16 (30) ◽  
pp. 5533-5538 ◽  
Author(s):  
Xuefeng He ◽  
Yongsu Li ◽  
Meng Wang ◽  
Hui-Xuan Chen ◽  
Bin Chen ◽  
...  
Keyword(s):  
Secondary Amine ◽  
Michael Addition ◽  
Cascade Reactions ◽  
Efficient Synthesis ◽  
Quaternary Carbon ◽  
Carbon Structure ◽  
Highly Efficient ◽  
Salicylic Acids

Employing salicylic acids and substituted 3-butyn-2-ones as the substrates, a morpholine catalyzed tandem dual Michael addition afforded a benzodioxin skeleton.

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>

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

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