Cu(II)-Promoted Methanolysis of N,N-Bis(2-picolyl)carbamates: Rate-Limiting Metal Ion Delivery of Coordinated Alcoholate Nucleophile Followed by Fast Partitioning of a Tetrahedral Intermediate-Reference-Cited by-同舟云学术

Cu(II)-Promoted Methanolysis of N,N-Bis(2-picolyl)carbamates: Rate-Limiting Metal Ion Delivery of Coordinated Alcoholate Nucleophile Followed by Fast Partitioning of a Tetrahedral Intermediate

Published:2015-01-14 Issue:3 Volume:80 Page:1357-1364
ISSN:0022-3263
Container-title:The Journal of Organic Chemistry
language:en
Short-container-title:J. Org. Chem.

Author:

Neverov Alexei A.¹,Cimpean Luana¹,Chiykowski Valerie¹,Vance Tyler¹,Brown R. Stan¹

Affiliation:

1. Department of Chemistry, Queen’s University, Kingston, Ontario K7L 3N6, Canada

Funder

Natural Sciences and Engineering Research Council of Canada

Queen's University

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry

Link

https://pubs.acs.org/doi/pdf/10.1021/jo5026496

Reference30 articles.

1. Cu(II)-Promoted Methanolysis of N,N-Dipicolylacetamide. Multistep Activation by Decoupling of >N̈–C═O Resonance via Cu(II)–N Binding, Delivery of the Cu(II):(−OCH3) Nucleophile, and Metal Ion Assistance of the Departure of the Leaving Group

2. Trifunctional Metal Ion-Catalyzed Solvolysis: Cu(II)-Promoted Methanolysis of N,N-bis(2-picolyl) Benzamides Involves Unusual Lewis Acid Activation of Substrate, Delivery of Coordinated Nucleophile, Powerful Assistance of the Leaving Group Departure

3. Rapid Ni, Zn, and Cu Ion-Promoted Alcoholysis of N,N-Bis(2-picolyl)- and N,N-Bis((1H-benzimidazol-2-yl)methyl)-p-nitrobenzamides in Methanol and Ethanol

4. Copper(II)-catalysis of the methanolysis and hydrolysis of NN-di-(2-pyridylmethyl)amides

5. The Activation of Tertiary Carboxamides in Metal Complexes: An Experimental and Theoretical Study on the Methanolysis of Acylated Bispicolylamine Copper(II) Complexes

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