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Metal Catalyzed C–H Functionalization

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (31 December 2021) | Viewed by 8344

Special Issue Editor


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Guest Editor
Department of Chemistry, Texas Tech University, Box 41061, Lubbock, TX, USA
Interests: transition metal catalysis; C–H functionalization; organic synthesis; green chemistry; electrochemistry; medicinal chemistry

Special Issue Information

Dear Colleagues, 

Metal-catalyzed direct C−H bond functionalization reactions represent one of the most efficient and environmentally friendly approaches in organic chemistry due to the avoidance of pre-functionalization of reaction precursors and minimization of metal waste. As a result, considerable efforts have been devoted to studying and advancing this research area over the past half-century, with particularly significant progress taking place in the last two decades. With the development of novel strategies and improved understanding of reaction mechanisms, both site- and stereo-selectivity can now be well controlled. Additionally, this approach has found applications in synthetic studies of natural products, medicinal compounds, materials, and agrochemicals. Considering the natural abundance of C−H bonds in organic molecules and high efficiency of this approach, it is clear that this research field will undoubtedly continue to expand and play an increasingly important role in organic synthesis. 

This Special Issue welcomes the submission of manuscripts that concentrate on the development of metal-catalyzed C−H bond functionalization reactions of aromatic or aliphatic substrates, mechanistic studies, or synthetic applications.

Prof. Dr. Haibo Ge
Guest Editor

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Keywords

  • Synthetic method
  • Catalysis
  • C−H functionalization
  • Metal
  • Organometallics

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Published Papers (3 papers)

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Research

11 pages, 12001 KiB  
Article
A Palladium-Catalyzed 4CzIPN-Mediated Decarboxylative Acylation Reaction of O-Methyl Ketoximes with α-Keto Acids under Visible Light
by Cheng Wang, Shan Yang, Zhibin Huang and Yingsheng Zhao
Molecules 2022, 27(6), 1980; https://doi.org/10.3390/molecules27061980 - 18 Mar 2022
Cited by 2 | Viewed by 2801
Abstract
This work presents a palladium-catalyzed oxime ether-directed ortho-selective benzoylation using benzoylformic acid as the acyl source with a palladium catalyst and 4CzIPN as the co-catalyst under light. Various non-symmetric benzophenone derivatives were obtained in moderate to good yields. A preliminary mechanism study revealed [...] Read more.
This work presents a palladium-catalyzed oxime ether-directed ortho-selective benzoylation using benzoylformic acid as the acyl source with a palladium catalyst and 4CzIPN as the co-catalyst under light. Various non-symmetric benzophenone derivatives were obtained in moderate to good yields. A preliminary mechanism study revealed that the reaction proceeds through a free radical pathway. Full article
(This article belongs to the Special Issue Metal Catalyzed C–H Functionalization)
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9 pages, 3511 KiB  
Article
Synthesis of Spiroindenyl-2-Oxindoles through Palladium-Catalyzed Spirocyclization of 2-Bromoarylamides and Vinyl Bromides
by Shuai Yang and Yanghui Zhang
Molecules 2021, 26(24), 7496; https://doi.org/10.3390/molecules26247496 - 10 Dec 2021
Cited by 1 | Viewed by 2290
Abstract
An expeditious approach to the construction of spiroindenyl-2-oxindoles was developed via a palladium-catalyzed spirocyclization reaction of 2-bromoarylamides with vinyl bromides. The reaction formed spiropalladacycles as the intermediates via carbopalladation and the C–H functionalization of 2-bromoarylamides. The spiropalladacycles reacted with vinyl bromides to form [...] Read more.
An expeditious approach to the construction of spiroindenyl-2-oxindoles was developed via a palladium-catalyzed spirocyclization reaction of 2-bromoarylamides with vinyl bromides. The reaction formed spiropalladacycles as the intermediates via carbopalladation and the C–H functionalization of 2-bromoarylamides. The spiropalladacycles reacted with vinyl bromides to form spiroindenyl-2-oxindoles. A Heck process rather than vinylic C–H functionalization was involved in the reaction. Full article
(This article belongs to the Special Issue Metal Catalyzed C–H Functionalization)
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11 pages, 3566 KiB  
Article
Palladium-Catalyzed C–H Arylation of Benzofurans with Triarylantimony Difluorides for the Synthesis of 2-Arylbenzofurans
by Yuki Kitamura, Yuki Murata, Mizuki Iwai, Mio Matsumura and Shuji Yasuike
Molecules 2021, 26(1), 97; https://doi.org/10.3390/molecules26010097 - 28 Dec 2020
Cited by 7 | Viewed by 2614
Abstract
Pd-catalyzed regioselective C–H arylation is a useful tool for the chemical modification of aromatic heterocycles and 2-arylbenzofuran derivatives are of interest as biologically active substances. Herein, the reaction of triarylantimony difluorides with benzofurans under aerobic conditions in 1,2-DCE, using 5 mol% Pd (OAc) [...] Read more.
Pd-catalyzed regioselective C–H arylation is a useful tool for the chemical modification of aromatic heterocycles and 2-arylbenzofuran derivatives are of interest as biologically active substances. Herein, the reaction of triarylantimony difluorides with benzofurans under aerobic conditions in 1,2-DCE, using 5 mol% Pd (OAc)2 and 2 eq. of CuCl2 at 80 °C, produced a variety of 2-arylbenzofurans in moderate-to-high yields. The reaction is sensitive to the electronic nature of the substituents on the benzene ring of the triarylantimony difluorides: an electron-donating group showed higher reactivity than an electron-withdrawing group. Single crystal X-ray analysis of tri(p-methylphenyl) antimony difluoride revealed that the central antimony atom exhibits trigonal bipyramidal geometry. Full article
(This article belongs to the Special Issue Metal Catalyzed C–H Functionalization)
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