Nickel-catalyzed enantioselective reductive conjugate arylation and heteroarylation via an elementary mechanism of 1,4-addition

Nickel-catalyzed enantioselective reductive conjugate arylation and heteroarylation via an elementary mechanism of 1,4-addition

A nickel complex of isoquinox promoted enantioselective conjugate arylation and heteroarylation of enones using aryl and heteroaryl halides directly. The reaction was successfully applied to stereoselective syntheses of ar-turmerone, chiral fragments of (+)-tolterodine and AZD5672. Mechanistically,...

Full description

Saved in:
Bibliographic Details
Main Authors: Zhang, Luoqiang, Zhao, Mengxin, Pu, Maoping, Ma, Zhaoming, Zhou, Jingsong, Chen, Caiyou, Wu, Yun-Dong, Chi, Robin Yonggui, Zhou, Jianrong Steve
Other Authors: School of Chemical and Biomedical Engineering
Format: Article
Language:English
Published: 2022
Subjects:
Science::Chemistry
Quaternary Stereogenic Centers
Arylboronic Acids
Online Access:https://hdl.handle.net/10356/163722
Tags: Add Tag
No Tags, Be the first to tag this record!
Institution: Nanyang Technological University
Language: English
id sg-ntu-dr.10356-163722
record_format dspace
spelling sg-ntu-dr.10356-1637222022-12-15T02:11:38Z Nickel-catalyzed enantioselective reductive conjugate arylation and heteroarylation via an elementary mechanism of 1,4-addition Zhang, Luoqiang Zhao, Mengxin Pu, Maoping Ma, Zhaoming Zhou, Jingsong Chen, Caiyou Wu, Yun-Dong Chi, Robin Yonggui Zhou, Jianrong Steve School of Chemical and Biomedical Engineering Science::Chemistry Quaternary Stereogenic Centers Arylboronic Acids A nickel complex of isoquinox promoted enantioselective conjugate arylation and heteroarylation of enones using aryl and heteroaryl halides directly. The reaction was successfully applied to stereoselective syntheses of ar-turmerone, chiral fragments of (+)-tolterodine and AZD5672. Mechanistically, experiments and calculations supported that an arylnickel(I) complex inserted to enones via an elementary 1,4-addition. National Research Foundation (NRF) We acknowledge financial support from Peking University Shenzhen Graduate School, State Key Laboratory of Chemical Oncogenomics, Guangdong Provincial Key Laboratory of Chemical Genomics, Shenzhen Bay Laboratory and Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs for J.S.Z., the National Natural Science Foundation of China (NSFC 21933004) for Y.D.W., and Singapore National Research Foundation (NRF-CRP22-2019-0002) for Y.R.C. 2022-12-15T02:11:38Z 2022-12-15T02:11:38Z 2022 Journal Article Zhang, L., Zhao, M., Pu, M., Ma, Z., Zhou, J., Chen, C., Wu, Y., Chi, R. Y. & Zhou, J. S. (2022). Nickel-catalyzed enantioselective reductive conjugate arylation and heteroarylation via an elementary mechanism of 1,4-addition. Journal of the American Chemical Society, 144(44), 20249-20257. https://dx.doi.org/10.1021/jacs.2c05678 0002-7863 https://hdl.handle.net/10356/163722 10.1021/jacs.2c05678 36315074 2-s2.0-85141493819 44 144 20249 20257 en NRF-CRP22-2019-0002 Journal of the American Chemical Society © 2022 American Chemical Society. All rights reserved.
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic Science::Chemistry
Quaternary Stereogenic Centers
Arylboronic Acids
spellingShingle Science::Chemistry
Quaternary Stereogenic Centers
Arylboronic Acids
Zhang, Luoqiang
Zhao, Mengxin
Pu, Maoping
Ma, Zhaoming
Zhou, Jingsong
Chen, Caiyou
Wu, Yun-Dong
Chi, Robin Yonggui
Zhou, Jianrong Steve
Nickel-catalyzed enantioselective reductive conjugate arylation and heteroarylation via an elementary mechanism of 1,4-addition
description A nickel complex of isoquinox promoted enantioselective conjugate arylation and heteroarylation of enones using aryl and heteroaryl halides directly. The reaction was successfully applied to stereoselective syntheses of ar-turmerone, chiral fragments of (+)-tolterodine and AZD5672. Mechanistically, experiments and calculations supported that an arylnickel(I) complex inserted to enones via an elementary 1,4-addition.
author2 School of Chemical and Biomedical Engineering
author_facet School of Chemical and Biomedical Engineering
Zhang, Luoqiang
Zhao, Mengxin
Pu, Maoping
Ma, Zhaoming
Zhou, Jingsong
Chen, Caiyou
Wu, Yun-Dong
Chi, Robin Yonggui
Zhou, Jianrong Steve
format Article
author Zhang, Luoqiang
Zhao, Mengxin
Pu, Maoping
Ma, Zhaoming
Zhou, Jingsong
Chen, Caiyou
Wu, Yun-Dong
Chi, Robin Yonggui
Zhou, Jianrong Steve
author_sort Zhang, Luoqiang
title Nickel-catalyzed enantioselective reductive conjugate arylation and heteroarylation via an elementary mechanism of 1,4-addition
title_short Nickel-catalyzed enantioselective reductive conjugate arylation and heteroarylation via an elementary mechanism of 1,4-addition
title_full Nickel-catalyzed enantioselective reductive conjugate arylation and heteroarylation via an elementary mechanism of 1,4-addition
title_fullStr Nickel-catalyzed enantioselective reductive conjugate arylation and heteroarylation via an elementary mechanism of 1,4-addition
title_full_unstemmed Nickel-catalyzed enantioselective reductive conjugate arylation and heteroarylation via an elementary mechanism of 1,4-addition
title_sort nickel-catalyzed enantioselective reductive conjugate arylation and heteroarylation via an elementary mechanism of 1,4-addition
publishDate 2022
url https://hdl.handle.net/10356/163722
_version_ 1753801105810128896

Similar Items