Late-Stage Transformation of Carboxylic Acids to N-Trifluoroethylimides with Trifluoromethyl Diazomethane-Reference-Cited by-同舟云学术

Late-Stage Transformation of Carboxylic Acids to N-Trifluoroethylimides with Trifluoromethyl Diazomethane

Published:2020-12-17 Issue:05 Volume:53 Page:961-970
ISSN:0039-7881
Container-title:Synthesis
language:en
Short-container-title:Synthesis

Author:

Hu Xiang-Guo¹²^ORCID,Qiu Xiao-Feng¹²,Liu De-Yong¹,Zhang Wen-Feng¹

Affiliation:

1. National Engineering Research Center for Carbohydrate Synthesis, Jiangxi Normal University

2. Key Laboratory of Small Functional Organic Molecule, Ministry of Education, Jiangxi Normal University

Abstract

AbstractWe report the first systematic evaluation of the reaction of trifluoromethyl diazomethane (2,2,2-trifluorodiazoethane, CF3CHN2) with drug-like molecules. We found our previous copper-catalyzed transformation of carboxylic acids to the corresponding N-trifluoroethylimides with CF3CHN2 and acetonitrile is well-suited for the late-stage modification of drug and drug-like acids. A procedure that enables the use of solid nitriles and nitriles with high boiling points as viable substrates is also disclosed.

Funder

Outstanding Young Talents Funding of Jiangxi Province

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Catalysis

Link

http://www.thieme-connect.de/products/ejournals/pdf/10.1055/a-1339-3227.pdf

Reference14 articles.

1. The medicinal chemist's toolbox for late stage functionalization of drug-like molecules

2. Copper-Catalyzed Late-Stage Benzylic C(sp3)–H Trifluoromethylation

3. Regioselective Cycloaddition of Trifluorodiazoethane with Electron-Deficient Allenic Esters and Ketones: Access to CF3-Substituted Pyrazolines and Pyrazoles

4. Silver(I)‐Catalyzed N ‐Trifluoroethylation of Anilines and O ‐Trifluoroethylation of Amides with 2,2,2‐Trifluorodiazoethane

Cited by 3 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Cu‐Catalyzed Reaction of Trifluoromethylated β‐Keto Diazos and Nitriles Proceeding via H₂O Addition to Nitrile Ylides;Advanced Synthesis & Catalysis;2024-07

2. Transition‐Metal‐Catalyzed Reactions Involving Trifluoro Diazo Compounds and Their Surrogates;European Journal of Organic Chemistry;2024-06-28

3. Copper-catalyzed multicomponent reaction of β-trifluoromethyl β-diazo esters enabling the synthesis of β-trifluoromethyl N,N-diacyl-β-amino esters;Beilstein Journal of Organic Chemistry;2024-02-02