Photo‐Catalyzed Stereospecific Synthesis of Trisubstituted Alkenes Incorporating 3,3‐Difluoro‐<i>γ</i>‐Lactams from Morita‐Baylis‐Hillman Acetates and <i>N</i>‐Allylbromodifluoroacetamides

Abstract A photocatalytic methodology has been devised for the stereoselective construction of trisubstituted alkenes incorporating 3,3‐difluoro‐γ‐lactams in 17–93% yields via a radical cascade process utilizing MBH acetates and N ‐allylbromodifluoroacetamides as starting materials. The reaction mechanism involves single‐electron transfer, 5 ‐ exo ‐ trig cyclization, radical addition, and elimination in a cascade fashion.

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Publication Details

Journal
Advanced Synthesis & Catalysis
Published
2024-10-31
DOI
https://doi.org/10.1002/adsc.202401103
Citations
6
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
1.25

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article

Photo‐Catalyzed Stereospecific Synthesis of Trisubstituted Alkenes Incorporating 3,3‐Difluoro‐γ‐Lactams from Morita‐Baylis‐Hillman Acetates and N‐Allylbromodifluoroacetamides

Xi Chen, Jianwu Liu, Hang‐Dong Zuo, Yue Zhang et al.
6 citations
Advanced Synthesis & Catalysis
Fluorine in Organic Chemistry
1.25
article

Photo‐Catalyzed Stereospecific Synthesis of Trisubstituted Alkenes Incorporating 3,3‐Difluoro‐γ‐Lactams from Morita‐Baylis‐Hillman Acetates and N‐Allylbromodifluoroacetamides

Xi Chen, Jianwu Liu, Hang‐Dong Zuo, Yue Zhang, Yuting Wang, Jia‐Yin Wang, Chi Ai
article en
6 citations

Abstract

Abstract A photocatalytic methodology has been devised for the stereoselective construction of trisubstituted alkenes incorporating 3,3‐difluoro‐γ‐lactams in 17–93% yields via a radical cascade process utilizing MBH acetates and N ‐allylbromodifluoroacetamides as starting materials. The reaction mechanism involves single‐electron transfer, 5 ‐ exo ‐ trig cyclization, radical addition, and elimination in a cascade fashion.

Advanced Synthesis & CatalysisVol. 367(2)
Changzhou University (CN)
Changzhou University
Openalex Percentile: Top 23%
Fluorine in Organic Chemistry
1.25
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Photo‐Catalyzed Stereospecific Synthesis of Trisubstituted Alkenes Incorporating 3,3‐Difluoro‐<i>γ</i>‐Lactams from Morita‐Baylis‐Hillman Acetates and <i>N</i>‐Allylbromodifluoroacetamides — Xi Chen, Jianwu Liu, et al. · Advanced Synthesis & Catalysis (2024) | TGRS Research Map | TGRS