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.

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

Simple and highly efficient catalyst- and waste-free ring opening of epoxides with Na2S in water

2010 ◽  
Vol 141 (3) ◽  
pp. 323-326 ◽  
Author(s):  
Najmedin Azizi ◽  
Elham Akbari ◽  
Frough Ebrahimi ◽  
Mohammad R. Saidi
Keyword(s):  
Ring Opening ◽  
Efficient Catalyst ◽  
Free Ring ◽  
Highly Efficient ◽  
Ring Opening Of Epoxides

ChemInform Abstract: Palladium-Catalyzed C(sp2)-H Bond Alkylation of Ketoximes by Using the Ring-Opening of Epoxides.

ChemInform ◽  
2016 ◽  
Vol 47 (46) ◽  
Author(s):  
Dan-Dan Li ◽  
Liang-Feng Niu ◽  
Zhi-Yu Ju ◽  
Zhihong Xu ◽  
Changzeng Wu
Keyword(s):  
Ring Opening ◽  
Palladium Catalyzed ◽  
Ring Opening Of Epoxides

Palladium-Catalyzed C(sp2)-H Bond Alkylation of Ketoximes by Using the Ring-Opening of Epoxides

2016 ◽  
Vol 2016 (18) ◽  
pp. 3090-3096 ◽  
Author(s):  
Dan-Dan Li ◽  
Liang-Feng Niu ◽  
Zhi-Yu Ju ◽  
Zhihong Xu ◽  
Changzeng Wu
Keyword(s):  
Ring Opening ◽  
Palladium Catalyzed ◽  
Ring Opening Of Epoxides

Investigation of the catalytic activity of an electron-deficient vanadium(IV) tetraphenylporphyrin: A new, highly efficient and reusable catalyst for ring-opening of epoxides

Polyhedron ◽  
2011 ◽  
Vol 30 (13) ◽  
pp. 2244-2252 ◽  
Author(s):  
S. Abdolmanaf Taghavi ◽  
Majid Moghadam ◽  
Iraj Mohammadpoor-Baltork ◽  
Shahram Tangestaninejad ◽  
Valiollah Mirkhani ◽  
...  
Keyword(s):  
Catalytic Activity ◽  
Ring Opening ◽  
Reusable Catalyst ◽  
Highly Efficient ◽  
Ring Opening Of Epoxides

Erbium(III) Triflate is a Highly Efficient Catalyst for the Synthesis of β-Alkoxy Alcohols, 1,2-Diols and β-Hydroxy Sulfides by Ring Opening of Epoxides

Synthesis ◽  
2009 ◽  
Vol 2009 (20) ◽  
pp. 3433-3438 ◽  
Author(s):  
Monica Nardi ◽  
Renato Dalpozzo ◽  
Manuela Oliverio ◽  
Rosina Paonessa ◽  
Antonio Procopio
Keyword(s):  
Ring Opening ◽  
Efficient Catalyst ◽  
Highly Efficient ◽  
Ring Opening Of Epoxides

Zirconyl triflate, [ZrO(OTf)2], as a new and highly efficient catalyst for ring-opening of epoxides

2009 ◽  
Vol 6 (4) ◽  
pp. 789-799 ◽  
Author(s):  
M. Moghadam ◽  
I. Mohammadpoor-Baltork ◽  
S. Tangestaninejad ◽  
V. Mirkhani ◽  
L. Shariati ◽  
...  
Keyword(s):  
Ring Opening ◽  
Efficient Catalyst ◽  
Highly Efficient ◽  
Ring Opening Of Epoxides

Electrophilic Ring Opening of Small Heterocycles

Synthesis ◽  
2017 ◽  
Vol 49 (24) ◽  
pp. 5307-5319 ◽  
Author(s):  
Chuan Wang
Keyword(s):  
Ethylene Oxide ◽  
Functional Groups ◽  
Organic Synthesis ◽  
Ring Opening ◽  
Building Blocks ◽  
Nickel Titanium ◽  
Ring Opening Reactions ◽  
Palladium Catalyzed ◽  
Ring Opening Of Epoxides ◽  
Nucleophilic Ring Opening

Small heterocycles, such as epoxides, aziridines, and ox­etanes are among the most useful building blocks in organic synthesis. Through electrophilic ring opening of these molecules, various electrophilic functional groups can be installed, which cannot be achieved via classic nucleophilic ring-opening reactions. In this review, the developments of electrophilic ring opening of small heterocycles are surveyed and organized according to the types of metal promoters.1 Introduction2 Electrophilic Ring Opening of Small Heterocycles Using Stoichiometric Metals2.1 Lithium-Mediated Electrophilic Ring Opening of Epoxides and Oxetanes2.2 Chromium-Mediated Electrophilic Ring Opening of Vinyl Epoxides2.3 Tin-Mediated Electrophilic Ring Opening of Vinyl Epoxides2.4 Samarium-Mediated Electrophilic Ring Opening of Vinyl and Alkynyl Epoxides2.5 Titanium-Mediated Electrophilic Ring Opening of Epoxides2.6 Platinum, Palladium, and Nickel-Mediated Electrophilic Ring Opening of 1,1-Dimethyl Ethylene Oxide3 Catalytic Electrophilic Ring Opening of Small Heterocycles3.1 Titanium-Catalyzed Electrophilic Ring Opening of Epoxides3.2 Palladium-Catalyzed Electrophilic Ring Opening of Vinyl and Alkynyl Small Heterocycles3.3 Iron-Catalyzed Electrophilic Ring Opening of Oxetanes3.4 Scandium-Catalyzed Electrophilic Ring Opening of Vinyl Epoxides3.5 Iridium-Catalyzed Electrophilic Ring Opening of 2-Methyl 2-Vinyl­oxiranes3.6 Nickel-Catalyzed Electrophilic Ring Opening of Epoxides and Aziridines3.7 Nickel–Titanium-Cocatalyzed Electrophilic Ring Opening of Epoxides4 Summary

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...

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