Issue 90, 2020
From the journal:

Chemical Communications

Nickel-catalyzed C-alkylation of thioamide, amides and esters by primary alcohols through a hydrogen autotransfer strategy†

Peng Yang, ORCID logo ‡*a   Xiuhua Wang,‡a   Yu Ma,a   Yaxin Sun,a   Li Zhang,a   Jieyu Yue,a   Kaiyue Fu,a   Jianrong Steve Zhou*b  and  Bo Tang ORCID logo *a  

* Corresponding authors

a College of Chemistry, Chemical Engineering and Materials Science, Collaborative Innovation Center of Functionalized Probes for Chemical Imaging in Universities of Shandong, Key Laboratory of Molecular and Nano Probes, Ministry of Education, Shandong Provincial Key Laboratory of Clean Production of Fine Chemicals, Shandong Normal University, Jinan, P. R. China
E-mail: yangpeng@sdnu.edu.cn, tangb@sdnu.edu.cn

b State Key Laboratory of Chemical Oncogenomics, Key Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Room F312, 2199 Lishui Road, Nanshan District, Shenzhen 518055, China
E-mail: jrzhou@pku.edu.cn

Abstract

A simple catalyst of Ni(OAc)2 and P(t-Bu)3 enables selective C-alkylation of thioacetamides and primary acetamides with alcohols for the first time. Monoalkylation of thioamides, amides and t-butyl esters occurs in excellent yields (>95%). Mechanistic studies reveal that the reaction proceeds via a hydrogen autotransfer pathway.

Graphical abstract: Nickel-catalyzed C-alkylation of thioamide, amides and esters by primary alcohols through a hydrogen autotransfer strategy

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/D0CC06468H
Article type
Communication
Submitted
26 Sep 2020
Accepted
14 Oct 2020
First published
15 Oct 2020

Chem. Commun., 2020,56, 14083-14086

Permissions

Request permissions

Nickel-catalyzed C-alkylation of thioamide, amides and esters by primary alcohols through a hydrogen autotransfer strategy

P. Yang, X. Wang, Y. Ma, Y. Sun, L. Zhang, J. Yue, K. Fu, J. S. Zhou and B. Tang, Chem. Commun., 2020, 56, 14083 DOI: 10.1039/D0CC06468H

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements