Synthesis of Multifunctional <i>α</i>,<i>α</i>‐Difluoroketones through Allylic Alkylation of Difluoroenoxysilanes with MBH Carbonates

Pan, Bowen; Shi, Yang; Tian, You‐Ping; Zhou, Jian; Yu, Jin‐Sheng

doi:10.1002/asia.202001145

Chemistry An Asian Journal

2020

DOI: 10.1002/asia.202001145

|View full text |Cite

Synthesis of Multifunctional α,α‐Difluoroketones through Allylic Alkylation of Difluoroenoxysilanes with MBH Carbonates

Bowen Pan

Yang Shi

You‐Ping Tian

et al.

Abstract: The first allylic alkylation of difluoroenoxysilanes with MBH carbonates catalyzed by triethylenediamine (DABCO) is developed, which allows rapid access to multifunctional α-gem-difluoroketones with up to 97% yields. Moreover, the gram-scale synthesis and the diversifying transformation of products to valuable gem-difluorinated molecules highlight the practicality of this methodology.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2021

2023

Publication Types

Select...

Article5

Relationship

Self Cite2

Independent3

Authors

Journals

Cited by 8 publications

References 106 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

HFIP‐Catalyzed Mannich Reaction: Divergent Synthesis of Difluoro‐Substituted 3,4‐Dihydroquinoxalin‐2(1H)‐ones and Monofluoroquinoxalin‐2(1H)‐ones

Xiong

Zhang

et al. 2023

Adv Synth Catal

View full text Add to dashboard Cite

Hexafluoroisopropanol (HFIP) has been extensively applied in organic synthesis as a versatile reaction media. However, the application of HFIP as an catalyst in organic synthesis has been rarely studied. Presented here, is the example of HFIP‐catalyzed Mannich‐type reaction between quinoxalin‐2(1H)‐ones and difluoroenoxysilanes. The developed protocol tolerates various substituents under mild reaction conditions, providing a divergent approach to the construction of difluoro‐substituted 3,4‐dihydroquinoxalin‐2(1H)‐ones and monofluoroquinoxalin‐2(1H)‐ones in 51–92% yields.

show abstract

HFIP‐Catalyzed Mannich Reaction: Divergent Synthesis of Difluoro‐Substituted 3,4‐Dihydroquinoxalin‐2(1H)‐ones and Monofluoroquinoxalin‐2(1H)‐ones

Xiong

Zhang

et al. 2023

Adv Synth Catal

View full text Add to dashboard Cite

show abstract

Catalyst-Free and Solvent-Controlled Divergent Synthesis of Difluoromethylene-Containing S-Heterocycles

Zhang

et al. 2021

J. Org. Chem.

Self Cite

View full text Add to dashboard Cite

An unprecedented catalyst-free reaction of benzo[b]thiophene-2,3-diones with difluoroenoxysilanes has been developed using either MeOH or H 2 O as the solvent, which constitutes a facile and efficient protocol for the solvent-controlled divergent synthesis of fiveand seven-membered S-heterocycles featuring a gem-difluoromethylene group. A gram-scale synthesis and the diversification of the product transformations to other difluorinated Sheterocycles further highlight its utility.

show abstract

Divergent Reaction of Activated Pyridines with α,α-Difluorinated gem-Diols: Regioselective Synthesis of gem-Difluorinated Dihydropyridines and Dihydropyridones

et al. 2022

View full text Add to dashboard Cite

The nucleophilic reactivity of α,α-difluorinated gem-diols toward activated pyridinium salts has been capitalized in a highly regioselective fashion, offering biologically relevant 1,4-dihydropyridines and 3,4-dihydro-2-pyridones adorned with the valuable gem-difluoromethylene motif. The protocol is scalable as well as high yielding and accommodates a broad range of substrates and functional groups. Additionally, the synthesis of difluorinated oxa-azabicyclo[3.3.1]nonane frameworks has been showcased through product diversification.

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Synthesis of Multifunctional α,α‐Difluoroketones through Allylic Alkylation of Difluoroenoxysilanes with MBH Carbonates

Cited by 8 publications

References 106 publications

HFIP‐Catalyzed Mannich Reaction: Divergent Synthesis of Difluoro‐Substituted 3,4‐Dihydroquinoxalin‐2(1H)‐ones and Monofluoroquinoxalin‐2(1H)‐ones

HFIP‐Catalyzed Mannich Reaction: Divergent Synthesis of Difluoro‐Substituted 3,4‐Dihydroquinoxalin‐2(1H)‐ones and Monofluoroquinoxalin‐2(1H)‐ones

Catalyst-Free and Solvent-Controlled Divergent Synthesis of Difluoromethylene-Containing S-Heterocycles

Divergent Reaction of Activated Pyridines with α,α-Difluorinated gem-Diols: Regioselective Synthesis of gem-Difluorinated Dihydropyridines and Dihydropyridones

Contact Info

Product

Resources

About