Copper(II) catalyzed heterobenzylic C(sp3)-H activation: Two efficient halogenation methodologies towards heterobenzyl halides

Bi, Wen‐Zhu; Qu, Chen; Chen, Xiao Lan; Wei, Sheng; Qu, Ling Bo; Liu, Shu Yun; Sun, Kai; Zhao, Yu

doi:10.1016/j.tet.2018.02.058

Cited by 11 publications

(5 citation statements)

References 53 publications

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“…Chen et al designed two simple and efficient strategies to access series of heterobenzyl halides. 101 They prepared large variety of 2-halomethylquinolines 238 from 2-methylquinolines 78 and TBHP via CuX (X ¼ I, Br, Cl) catalyzed one-pot reaction (Scheme 90). Inspired from the results of rst method, they developed a second protocol in which 2-methylheterocycles 239 and iodine were reacted in the presence of CuSO 4 $5H 2 O to form 250 was established.…”

Section: Miscellaneousmentioning

confidence: 99%

Progress and prospects in copper-catalyzed C–H functionalization

et al. 2020

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Section: Miscellaneousmentioning

confidence: 99%

Progress and prospects in copper-catalyzed C–H functionalization

et al. 2020

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“…Chen and co-workers developed a practical and simple synthetic methodology towards various heterobenzyl halides by using CuX (X = I, Br, Cl) and TBHP in MeCN (Scheme 61). 52 Traditional methods for the halogenation at the heterobenzyl position with NCS, NBS, or NIS result in mixtures of monohalogenated product and dihalogenated side product. However, in this CuX-mediated halogenation, only the monohalogenated product was observed.…”

Section: Scheme 59 Copper-catalyzed Tandem N-acylation and C 5 -H Halmentioning

confidence: 99%

Recent Advances in Copper(II)-Mediated or -Catalyzed C–H Functionalization

Jia

Yin

2018

Synthesis

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This review summarizes recent developments in the field of copper-mediated or -catalyzed C–H functionalization. The substrate scope has been expanded from the C–H activation of aryls to more challenging alkyls. Furthermore, catalytic amounts of copper salt are sufficient to promote the challenging C–H functionalization in some cases, which represents the focus of future research.1 Introduction2 C–C Bond Formation3 C–N Bond Formation4 C–O Bond Formation5 C–Halogen Bond Formation6 C–S Bond Formation7 Conclusions and Outlook

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“…Chen and co-workers developed CuX-mediated selective monohalogenation of 2methylquinolines producing corresponding heterobenzyl halides [51] (Scheme 13). It should be noted that traditional methods for halogenation at the heterobenzyl position with NCS, NBS, or NIS result in mixtures of the monohalogenated product and the dihalogenated side product.…”

mentioning

confidence: 99%

“…It should be noted that traditional methods for halogenation at the heterobenzyl position with NCS, NBS, or NIS result in mixtures of the monohalogenated product and the dihalogenated side product. Chen and co-workers developed CuX-mediated selective monohalogenation of 2methylquinolines producing corresponding heterobenzyl halides [51] (Scheme 13). It should be noted that traditional methods for halogenation at the heterobenzyl position with NCS, NBS, or NIS result in mixtures of the monohalogenated product and the dihalogenated side product.…”

mentioning

confidence: 99%

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The Influence of Copper on Halogenation/Dehalogenation Reactions of Aromatic Compounds and Its Role in the Destruction of Polyhalogenated Aromatic Contaminants

Weidlich

2021

Catalysts

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The effect of copper and its compounds on halogenation and dehalogenation of aromatic compounds will be discussed in the proposed article. Cu oxidized to appropriate halides is an effective halogenation catalyst not only for the synthesis of halogenated benzenes or their derivatives as desired organic fine chemicals, but is also an effective catalyst for the undesirable formation of thermodynamically stable and very toxic polychlorinated and polybrominated aromatic compounds such as polychlorinated biphenyls, dibenzo-p-dioxins and dibenzofurans accompanied incineration of waste contaminated with halogenated compounds or even inorganic halides. With appropriate change in reaction conditions, copper and its alloys or oxides are also able to effectively catalyze dehalogenation reactions, as will be presented in this review.

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Copper(II) catalyzed heterobenzylic C(sp3)-H activation: Two efficient halogenation methodologies towards heterobenzyl halides

Cited by 11 publications

References 53 publications

Progress and prospects in copper-catalyzed C–H functionalization

Progress and prospects in copper-catalyzed C–H functionalization

Recent Advances in Copper(II)-Mediated or -Catalyzed C–H Functionalization

The Influence of Copper on Halogenation/Dehalogenation Reactions of Aromatic Compounds and Its Role in the Destruction of Polyhalogenated Aromatic Contaminants

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