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Literature DB >> 33651602

Click Chemistry with Cyclopentadiene.

Abstract

Cyclopentadiene is one of the most reactive dienes in normal electron-demand Diels-Alder reactions. The high reactivities and yields of cyclopentadiene cycloadditions make them ideal as click reactions. In this review, we discuss the history of the cyclopentadiene cycloaddition as well as applications of cyclopentadiene click reactions. Our emphasis is on experimental and theoretical studies on the reactivity and stability of cyclopentadiene and cyclopentadiene derivatives.

Entities: Chemical Disease Species

Year: 2021 PMID： 33651602 PMCID： PMC8222071 DOI： 10.1021/acs.chemrev.0c01055

Source DB: PubMed Journal: Chem Rev ISSN： 0009-2665 Impact factor: 60.622

83 in total

1. Chemistry of the fullerenes: the manifestation of strain in a class of continuous aromatic molecules.

Authors: R C Haddon
Journal: Science Date: 1993-09-17 Impact factor: 47.728

2. Origins of the Unfavorable Activation and Reaction Energies of 1-Azadiene Heterocycles Compared to 2-Azadiene Heterocycles in Diels-Alder Reactions.

Authors: Jason S Fell; Blanton N Martin; K N Houk
Journal: J Org Chem Date: 2017-02-09 Impact factor: 4.354

3. Regioselective exohedral functionalization of La@C82 and its 1,2,3,4,5-pentamethylcyclopentadiene and adamantylidene adducts.

Authors: Yutaka Maeda; Satoru Sato; Koji Inada; Hidefumi Nikawa; Michio Yamada; Naomi Mizorogi; Tadashi Hasegawa; Takahiro Tsuchiya; Takeshi Akasaka; Tatsuhisa Kato; Zdenek Slanina; Shigeru Nagase
Journal: Chemistry Date: 2010-02-15 Impact factor: 5.236

4. Triazolinediones as Highly Enabling Synthetic Tools.

Authors: Kevin De Bruycker; Stijn Billiet; Hannes A Houck; Subrata Chattopadhyay; Johan M Winne; Filip E Du Prez
Journal: Chem Rev Date: 2016-02-22 Impact factor: 60.622

5. Hyperconjugative Antiaromaticity Activates 4H-Pyrazoles as Inverse-Electron-Demand Diels-Alder Dienes.

Authors: Brian J Levandowski; Nile S Abularrage; K N Houk; Ronald T Raines
Journal: Org Lett Date: 2019-10-07 Impact factor: 6.005

6. Purification of endohedral trimetallic nitride fullerenes in a single, facile step.

Authors: Zhongxin Ge; James C Duchamp; Ting Cai; Harry W Gibson; Harry C Dorn
Journal: J Am Chem Soc Date: 2005-11-23 Impact factor: 15.419

7. Aromaticity interplay between quinodimethanes and C(60) in diels-alder reactions: insights from a theoretical study

Authors:
Journal: J Org Chem Date: 2000-09-22 Impact factor: 4.354

8. A Diene-Containing Noncanonical Amino Acid Enables Dual Functionality in Proteins: Rapid Diels-Alder Reaction with Maleimide or Proximity-Based Dimerization.

Authors: Andre H St Amant; Fengying Huang; Jia Lin; Keith Rickert; Vaheh Oganesyan; Daniel Lemen; Shenlan Mao; Jay Harper; Marcello Marelli; Herren Wu; Changshou Gao; Javier Read de Alaniz; R James Christie
Journal: Angew Chem Int Ed Engl Date: 2019-05-14 Impact factor: 15.336

Click Chemistry with Cyclopentadiene.

1. Chemistry of the fullerenes: the manifestation of strain in a class of continuous aromatic molecules.

2. Origins of the Unfavorable Activation and Reaction Energies of 1-Azadiene Heterocycles Compared to 2-Azadiene Heterocycles in Diels-Alder Reactions.

3. Regioselective exohedral functionalization of La@C82 and its 1,2,3,4,5-pentamethylcyclopentadiene and adamantylidene adducts.

4. Triazolinediones as Highly Enabling Synthetic Tools.

5. Hyperconjugative Antiaromaticity Activates 4H-Pyrazoles as Inverse-Electron-Demand Diels-Alder Dienes.

6. Purification of endohedral trimetallic nitride fullerenes in a single, facile step.

7. Aromaticity interplay between quinodimethanes and C(60) in diels-alder reactions: insights from a theoretical study

8. A Diene-Containing Noncanonical Amino Acid Enables Dual Functionality in Proteins: Rapid Diels-Alder Reaction with Maleimide or Proximity-Based Dimerization.

9. Covalently patterned graphene surfaces by a force-accelerated Diels-Alder reaction.

10. Secondary Orbital Interactions Enhance the Reactivity of Alkynes in Diels-Alder Cycloadditions.

1. Gold-Catalyzed Regioselective Synthesis of Crowded Cyclopentadienes by Migratory Cycloisomerization of Vinylallenes.

2. Geminal Repulsion Disrupts Diels-Alder Reactions of Geminally Substituted Cyclopentadienes and 4H-Pyrazoles.