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

Photocatalytic Hydrazonyl Radical-Mediated Radical Cyclization/Allylation Cascade: Synthesis of Dihydropyrazoles and Tetrahydropyridazines
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光催化腙自由基介导的自由基环化/烯丙基化级联:二氢吡唑和四氢哒嗪的合成

DOI:
10.1021/acs.orglett.7b01609
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发表时间:
2017
期刊:
影响因子:
5.2
通讯作者:
Wen-Jing Xiao
Wen-Jing Xiao
中科院分区:
化学1区
文献类型:
--
作者:
Quan-Qing Zhao;Jun Chen;Dong-Mei Yan;Jia-Rong Chen;Wen-Jing Xiao

文献摘要

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以烯丙基砜和Morita-Baylis-Hillman加成物为烯丙基源,发展了一种新型的光催化腙基自由基介导的β,γ-不饱和腙的自由基环化/烯丙基化级联反应,该反应提供了一种高效、实用的合成二氢吡唑和四氢哒嗪的途径.该反应是通过可控生成的腙基自由基通过氧化去质子化电子转移策略和选择性捕获的所得的C-中心的自由基在可见光照射下,使。
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.