Chiral Arylated Amines via C-N Coupling of Chiral Amines with Aryl Bromides Promoted by Light



Song, Geyang, Yang, Liu, Li, Jing-Sheng, Tang, Wei-Jun, Zhang, Wei, Cao, Rui, Wang, Chao, Xiao, Jianliang ORCID: 0000-0003-2010-247X and Xue, Dong
(2021) Chiral Arylated Amines via C-N Coupling of Chiral Amines with Aryl Bromides Promoted by Light. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 60 (39). pp. 21536-21542.

[img] Text
Manuscript.pdf - Author Accepted Manuscript

Download (1MB) | Preview

Abstract

The Buchwald-Hartwig C-N coupling reaction has found widespread applications in organic synthesis. Over the past two decades or so, many improved catalysts have been introduced, allowing various amines and aryl electrophiles to be readily used nowadays. However, there lacks a protocol that could be used to couple a wide range of chiral amines and aryl halides, without erosion of the enantiomeric excess (ee). Reported in this article is a method based on molecular Ni catalysis driven by light, which enables stereoretentive C-N coupling of optically active amines, amino alcohols, and amino acid esters with aryl bromides, with no need for any external photosensitizer. The method is effective for a wide variety of coupling partners, including those bearing functional groups sensitive to bases and nucleophiles, thus providing a viable alternative to accessing synthetically important chiral N-aryl amines, amino alcohols, and amino acids esters. Its viability is demonstrated by 92 examples with up to 99 % ee.

Item Type: Article
Uncontrolled Keywords: chiral N-aryl amines, chiral N-aryl amino acids, chiral N-aryl amino alcohols, C-N coupling, nickel catalysis
Divisions: Faculty of Science and Engineering > School of Physical Sciences
Depositing User: Symplectic Admin
Date Deposited: 19 Jul 2021 07:59
Last Modified: 18 Jan 2023 21:35
DOI: 10.1002/anie.202108587
Related URLs:
URI: https://livrepository.liverpool.ac.uk/id/eprint/3130488