Literature DB >> 28640626

Photocatalytic Hydrazonyl Radical-Mediated Radical Cyclization/Allylation Cascade: Synthesis of Dihydropyrazoles and Tetrahydropyridazines.

Quan-Qing Zhao1, Jun Chen1, Dong-Mei Yan1, Jia-Rong Chen1, Wen-Jing Xiao1,2.   

Abstract

A novel photocatalytic hydrazonyl radical-mediated radical cyclization/allylation cascade reaction of β,γ-unsaturated hydrazones is developed using allyl sulfones and Morita-Baylis-Hillman adduct as allyl sources, which provides an efficient and practical access to various diversely functionalized dihydropyrazoles and tetrahydropyridazines. The reaction is enabled by controllable generation of hydrazonyl radicals via an oxidative deprotonation electron transfer strategy and selective trapping of the resultant C-centered radicals under visible light irradiation.

Entities:  

Year:  2017        PMID: 28640626     DOI: 10.1021/acs.orglett.7b01609

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  7 in total

Review 1.  Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

Authors:  Philip R D Murray; James H Cox; Nicholas D Chiappini; Casey B Roos; Elizabeth A McLoughlin; Benjamin G Hejna; Suong T Nguyen; Hunter H Ripberger; Jacob M Ganley; Elaine Tsui; Nick Y Shin; Brian Koronkiewicz; Guanqi Qiu; Robert R Knowles
Journal:  Chem Rev       Date:  2021-11-23       Impact factor: 60.622

Review 2.  Strategies to Generate Nitrogen-centered Radicals That May Rely on Photoredox Catalysis: Development in Reaction Methodology and Applications in Organic Synthesis.

Authors:  Kitae Kwon; R Thomas Simons; Meganathan Nandakumar; Jennifer L Roizen
Journal:  Chem Rev       Date:  2021-10-08       Impact factor: 60.622

3.  Brønsted acid-promoted hydroamination of unsaturated hydrazones: access to biologically important 5-arylpyrazolines.

Authors:  Han He; Ning Xu; Honglin Zhang; Bin Chen; Zhengnan Hu; Kang Guo; Jianlin Chun; Shujun Cao; Yingguang Zhu
Journal:  RSC Adv       Date:  2021-05-11       Impact factor: 4.036

4.  Arene dearomatization through a catalytic N-centered radical cascade reaction.

Authors:  Rory C McAtee; Efrey A Noten; Corey R J Stephenson
Journal:  Nat Commun       Date:  2020-05-20       Impact factor: 14.919

5.  Formal [4 + 1] cycloaddition of in situ generated 1,2-diaza-1,3-dienes with diazo esters: facile approaches to dihydropyrazoles containing a quaternary center.

Authors:  Bo Chen; Wen-Dao Chu; Quan-Zhong Liu
Journal:  RSC Adv       Date:  2019-01-11       Impact factor: 4.036

6.  Direct transfer of tri- and di-fluoroethanol units enabled by radical activation of organosilicon reagents.

Authors:  Xiang Chen; Xingxing Gong; Zhengyu Li; Gang Zhou; Zhihong Zhu; Weilu Zhang; Shanshan Liu; Xiao Shen
Journal:  Nat Commun       Date:  2020-06-02       Impact factor: 14.919

7.  Mn- and Co-Catalyzed Aminocyclizations of Unsaturated Hydrazones Providing a Broad Range of Functionalized Pyrazolines.

Authors:  Moritz Balkenhohl; Sebastian Kölbl; Tony Georgiev; Erick M Carreira
Journal:  JACS Au       Date:  2021-06-11
  7 in total

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