A mechanistic investigation into N-heterocyclic carbene (NHC) catalyzed umpolung of ketones and benzonitriles: is the cyano group better than the classical carbonyl group for the addition of NHC?
Author:
Affiliation:
1. Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis
2. Faculty of Chemistry Northeast Normal University
3. Changchun
4. 130024 China
Abstract
The cooperative participation of NHC-H2O-activated cyano carbon is more preferred than the classical NHC-activated carbonyl carbon.
Funder
National Natural Science Foundation of China
Publisher
Royal Society of Chemistry (RSC)
Subject
Organic Chemistry
Link
http://pubs.rsc.org/en/content/articlepdf/2019/QO/C8QO01309H
Reference67 articles.
1. Insights into Stereoselective Aminomethylation Reaction of α,β-Unsaturated Aldehyde with N,O-Acetal via N-Heterocyclic Carbene and Brønsted Acid/Base Cooperative Organocatalysis
2. Importance of Electrostatic Effects in the Stereoselectivity of NHC-Catalyzed Kinetic Resolutions
3. Merging N-Heterocyclic Carbene Catalysis and Single Electron Transfer: A New Strategy for Asymmetric Transformations
4. Highly Regio- and Stereodivergent Access to 1,2-Amino Alcohols or 1,4-Fluoro Alcohols by NHC-Catalyzed Ring Opening of Epoxy enals
5. An overview of N-heterocyclic carbenes
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