Cu/N,N′-Dibenzyloxalamide-Catalyzed N-Arylation of Heteroanilines
Authors:
- 15 August 2019
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 21 (17) , 6874-6878
Abstract
N,N′-Dibenzyloxalamide (DBO) was identified as a powerful ligand for promoting Cu-catalyzed coupling of heteroanilines with (hetero)aryl halides. For (hetero)aryl chlorides, the coupling reaction occurred at 130 °C with 5 mol % CuBr and 10 mol % DBO. For (hetero)aryl bromides/iodides, coupling reaction took place at 80–100 °C with 1 mol % CuI and 2 mol % DBO. A variety of heteroanilines worked well to afford the arylation products in good to excellent yields.Keywords
Funding Information
- National Natural Science Foundation of China (21831009, 21621002)
- Chinese Academy of Sciences (XDB20020200, QYZDJ-SSW-SLH029)
This publication has 46 references indexed in Scilit:
- Buchwald-Hartwig reaction: An overviewJournal of Organometallic Chemistry, 2018
- Kinase inhibitors: the road aheadNature Reviews Drug Discovery, 2018
- Selected Copper‐Based Reactions for C−N, C−O, C−S, and C−C Bond FormationAngewandte Chemie International Edition, 2017
- Advances of small molecule targeting of kinasesCurrent Opinion in Chemical Biology, 2017
- An Improved Synthesis of the Free Base and Diglycolate Salt of CEP-33779; A Janus Kinase 2 InhibitorOrganic Process Research & Development, 2016
- Applications of Palladium-Catalyzed C–N Cross-Coupling ReactionsChemical Reviews, 2016
- Small-molecule kinase inhibitors: an analysis of FDA-approved drugsDrug Discovery Today, 2016
- FDA-approved small-molecule kinase inhibitorsTrends in Pharmacological Sciences, 2015
- Synthesis, Structure–Activity Relationships, and in Vivo Efficacy of the Novel Potent and Selective Anaplastic Lymphoma Kinase (ALK) Inhibitor 5-Chloro-N2-(2-isopropoxy-5-methyl-4-(piperidin-4-yl)phenyl)-N4-(2-(isopropylsulfonyl)phenyl)pyrimidine-2,4-diamine (LDK378) Currently in Phase 1 and Phase 2 Clinical TrialsJournal of Medicinal Chemistry, 2013
- Transition metal-catalyzed N-arylations of amidines and guanidinesChemical Society Reviews, 2012