The importance of N-heterocyclic carbene basicity in organocatalysis

Literature Information

Publication Date 2018-09-07
DOI 10.1039/C8OB01667D
Impact Factor 3.876
Authors

Ning Wang, Jiahui Xu, Jeehiun K. Lee


View Original

Abstract

N-Heterocyclic carbenes (NHCs) are versatile species that figure prominently as catalysts. Despite their widespread use in organocatalysis, studies of the relationship between the basicity of NHCs and their catalytic ability are limited. Herein we review work on both the examination of NHC basicity as well as its impact on organocatalysis. The review is divided into three main parts: an overview of NHC basicity studies, both in solution and in the gas phase; the role of basicity in Umpolung-type catalysis; and the relationship between NHC basicity and its growing role as a Brønsted base catalyst. This review is not an exhaustive catalog of all NHC catalysis, but rather focuses on work that specifically examines and discusses the effect of NHC basicity on catalyst function.

Related Literature

Correction: Catalytic aerobic oxidation of renewable furfural to maleic anhydride and furanone derivatives with their mechanistic studies

Jihong Lan, Zhuqi Chen, Jinchi Lin, Guochuan Yin

2014-09-10 Correction

DOI: 10.1039/C4GC90039A

Fermentation of hydrolysate detoxified by pervaporation through block copolymer membranes

Douglas R. Greer, Thalita P. Basso, Ana B. Ibanez, Stefan Bauer, Jeffrey M. Skerker, A. Evren Ozcam, Dacia Leon, Chaeyoung Shin, Adam P. Arkin

2014-07-11 Paper

DOI: 10.1039/C4GC00756E

Influence of precursor type on non-toxic hybrid inks for high-efficiency Cu2ZnSnS4 thin-film solar cells

Kyujin Kim, Inhyuk Kim, Yunjung Oh, Daehee Lee, Kyoohee Woo, Sunho Jeong, Jooho Moon

2014-07-10 Paper

DOI: 10.1039/C4GC00896K

Rational investigations in the ring opening of cyclic carbonates by amines

L. Jean-Gérard, R. Auvergne, D. Benazet, S. Caillol, B. Andrioletti

2014-07-16 Paper

DOI: 10.1039/C4GC01032A

A nickel doped perovskite catalyst for reforming methane rich biogas with minimal carbon deposition

Samuel E. Evans, John Z. Staniforth, Richard J. Darton, R. Mark Ormerod

2014-07-31 Paper

DOI: 10.1039/C4GC00782D

General and selective reductive amination of carbonyl compounds using a core–shell structured Co3O4/NGr@C catalyst

Tobias Stemmler, Felix A. Westerhaus, Annette-Enrica Surkus, Marga-Martina Pohl, Kathrin Junge, Matthias Beller

2014-07-29 Communication

DOI: 10.1039/C4GC00536H

Fluoro-functionalized polymeric ionic liquids: highly efficient catalysts for CO2 cycloaddition to cyclic carbonates under mild conditions

Zhen-Zhen Yang, Yanfei Zhao, Guipeng Ji, Hongye Zhang, Bo Yu, Xiang Gao, Zhimin Liu

2014-06-06 Communication

DOI: 10.1039/C4GC00730A

Lactic acid production from glucose over polymer catalysts in aqueous alkaline solution under mild conditions

Xincheng Wang, Yanlei Song, Chongpin Huang, Fengbing Liang, Biaohua Chen

2014-06-26 Paper

DOI: 10.1039/C4GC00811A

A recoverable Pd nanocatalyst for selective semi-hydrogenation of alkynes: hydrogenation of benzyl-propargylamines as a challenging model

Paula M. Uberman, Natalia J. S. Costa, Rafaela C. Carmona, Alcindo A. Dos Santos, Liane M. Rossi

2014-07-22 Paper

DOI: 10.1039/C4GC00669K

Synthesis of metal–organic frameworks by continuous flow

Peter A. Bayliss, Eduardo Pérez, Sihai Yang, Chiu C. Tang, Martyn Poliakoff, Martin Schröder

2014-06-06 Paper

DOI: 10.1039/C4GC00313F

You might also like

Compound Q&A

How should 2-Methylbenzene-1,4-diamine dihydrochloride (CAS: 615-45-2) be stored?

2-Methylbenzene-1,4-diamine dihydrochloride (CAS: 615-45-2) should be stored in ...

615-45-22-Methylbenzene-1,4-...
Compound Q&A

Is (1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide (CAS: 132747-20-7) safe?

(1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide is generally considered sa...

132747-20-7(1S,4S)-2,5-Diazabic...
Compound Q&A

What industries use (6-Chloropyridazin-3-YL)methanamine (CAS: 871826-15-2)?

(6-Chloropyridazin-3-YL)methanamine finds applications in the pharmaceutical ind...

871826-15-2(6-Chloropyridazin-3...
Compound Q&A

What are the main uses of 2-Fluoro-3-methylphenol (CAS: 77772-72-6)?

2-Fluoro-3-methylphenol is primarily used in the synthesis of pharmaceuticals, p...

77772-72-62-Fluoro-3-methylphe...
Compound Q&A

What precautions should be taken when handling 3-Methoxy-4-nitrobenzonitrile (CAS: 177476-75-4)?

When handling 3-Methoxy-4-nitrobenzonitrile, it is important to wear appropriate...

177476-75-43-Methoxy-4-nitroben...
Compound Q&A

What precautions should be taken when handling 1,3-Oxazolo[4,5-b]pyridine-2(3H)-thione (CAS: 211949-57-4)?

When handling 1,3-Oxazolo[4,5-b]pyridine-2(3H)-thione (CAS: 211949-57-4), it is ...

211949-57-4[1,3]Oxazolo[4,5-b]p...
Compound Q&A

What regulatory guidelines apply to 4-Ethynylbenzamide (CAS: 90347-86-7)?

4-Ethynylbenzamide (CAS: 90347-86-7) falls under various regulatory guidelines i...

90347-86-74-Ethynylbenzamide
Compound Q&A

What are the main uses of 3-(2-Ethylphenyl)-2-thioxo-4-imidazolidinone (CAS: 186822-57-1)?

3-(2-Ethylphenyl)-2-thioxo-4-imidazolidinone is primarily used as an intermediat...

186822-57-13-(2-Ethylphenyl)-2-...
Compound Q&A

What is (2-Fluoro-6-methoxyphenyl)acetic acid (CAS: 500912-19-6)?

(2-Fluoro-6-methoxyphenyl)acetic acid, also known as 4-fluoro-3-methoxybenzoic a...

500912-19-6(2-Fluoro-6-methoxyp...
Compound Q&A

What is the market or research trend for 2-[4-(Hydroxymethyl)phenoxy]ethanol (CAS: 102196-18-9)?

Market trends for 2-[4-(Hydroxymethyl)phenoxy]ethanol (CAS: 102196-18-9) indicat...

102196-18-92-[4-(Hydroxymethyl)...

Source Journal

Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
CiteScore: 3.4
Self-citation Rate: 10.3%
Articles per Year: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.