Synthesis of Polychloromethyl-Containing Indolines via Metal-Free Radical Arylpolychloromethylation of Unactivated Alkenes

Li, Wenlan; Sun, Yitong; Yao, Yongchao; Xu, Ying; Li, Peng; Liu, Yingjie; Liang, Deqiang

doi:10.6023/cjoc201901047

Cited by 5 publications

(2 citation statements)

References 7 publications

(8 reference statements)

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“…该方法以过氧化苯甲酰(BPO)为氧化剂, 氯仿和二氯甲烷分别为三氯甲基和二氯甲基自由基源, 无需金属催化剂, 以较好的收率获得了多氯甲基化 2-吲哚酮化合物, 底物适用范围较广. 2022 年, 权正军等 [10] 2019 年, 刘颖杰课题组 [13] 发展了一种无金属催化 N-烯丙基芳胺与氯仿的三氯甲基化/环化反应(Scheme 杂芳羧酸酯普遍存在于众多功能分子结构中. 在过去的几十年中, 随着有机金属化学的快速发展, 杂芳烃的烷氧羰基化取得了巨大的进展, 并且与羧酸衍生物的传统酯化相比, 该方法已经成为建立羧酸酯的替代方法 [15] .…”

Section: 三氯甲基自由基unclassified

Research Progress in Radical Addition Reaction of Alkenes Involving Chloroform

Zhang,

et al. 2023

Chinese Journal of Organic Chemistry

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Polyhalomethyl compounds, especially those with dichloromethyl or trichloromethyl structures, are widely used in fields, such as medicine, agriculture and organic functional materials. In addition, polychloromethyl could also be easily converted into various functional groups, such as amino, hydroxyl, carboxyl and carbonyl groups, which could be further used to construct complex ring structures. Therefore, the development of effective polychlorinated methylation strategies has important research significance in the synthesis of many natural molecules with biological activities. Chloroform is an easily available chemical resource that can undergo free radical transformation in the presence of free radical initiators, forming •CCl3 radical through hydrogen atom transfer (HAT) and •CHCl2 radical through halogen atom transfer (XAT). According to the different types of free radicals produced by chloroform, the latest research progress of chloroform participating radical addition of alkenes to construct polychloromethyl substituted compounds is summarized, and the reaction range, limitations and some mechanisms are also discussed.

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Section: 三氯甲基自由基unclassified

Research Progress in Radical Addition Reaction of Alkenes Involving Chloroform

Zhang,

et al. 2023

Chinese Journal of Organic Chemistry

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“…In 2019, Liang and co‐workers also developed a similar procedure towards polychloromethyl‐containing indolines with dicumyl peroxide (DCP) as the initiator at 120 °C [21] . The reaction runs relatively much quickly, which can be finished within 3 h (eq 7).…”

Section: Di‐ and Trichloromethylation Using Polyhalomethanes As The Pmentioning

confidence: 99%

Recent Advances in Polychloromethylation Reactions

Huang

Pan

2020

Adv Synth Catal

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Molecules with di‐ or trichloromethyl group are widely existed in natural products and man‐made structures that represent special activities in pharmaceuticals and agrochemicals. Besides, polychloromethyl‐containing compounds are also high valuable intermediates in organic synthesis and also can be used as functional materials. Therefore, significant efforts have been made toward the incorporation of polychloromethyl groups into certain structures. In this field, a variety of polychloromethyl reagents, such as CH2Cl2, HCCl3, CCl4, TMSCCl3, TMSCCl2H, etc. have been utilized as the di‐ or trichloromethyl sources toward polychloromethylated structures through radical, nucleophilic, and other reaction patterns. In this review, we summarized and discussed the recent achievements in the synthesis of polychloromethylated compounds, mainly focused on the employment of different polychloromethyl reagents. Most of the works we investigated were reported after 2010. Mechanism discussions and outlooks were also given.

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