Dehydrogenative Coupling Reactions with Oxidized Guanidino-Functionalized Aromatic Compounds: Novel Options for σ-Bond Activation

2016 ◽  
Vol 22 (34) ◽  
pp. 11971-11976 ◽  
Author(s):  
Ute Wild ◽  
Stefanie Federle ◽  
Arne Wagner ◽  
Elisabeth Kaifer ◽  
Hans-Jörg Himmel
Keyword(s):  
Aromatic Compounds ◽  
Bond Activation ◽  
Coupling Reactions ◽  
Dehydrogenative Coupling

Identifications and electronic characterizations of four cyclodehydrogenation products of H2TPP molecules on Au(111)

2021 ◽  
Author(s):  
Jianchen Lu ◽  
Binbin Da ◽  
Wei Xiong ◽  
Renjun Du ◽  
Zhenliang Hao ◽  
...  
Keyword(s):  
Atomic Force Microscopy ◽  
Scanning Tunneling Microscopy ◽  
Bond Activation ◽  
Scanning Tunneling ◽  
Coupling Reactions ◽  
Tunneling Microscopy ◽  
Force Microscopy ◽  
Atomic Force ◽  
Dehydrogenative Coupling

C–H bond activation and dehydrogenative coupling reactions have always been significant approaches to construct microscopic nanostructures on surfaces. By using scanning tunneling microscopy/spectroscopy (STM/STS) and non-contact atomic force microscopy (nc-AFM)...

scholarly journals Copper-Catalyzed Direct Alkylation of Perfluoroarenes with Hydrocarbons

2019 ◽  
Author(s):  
Weilong Xie ◽  
Joon Heo ◽  
Dongwook Kim ◽  
Sukbok Chang
Keyword(s):  
Bond Activation ◽  
Copper Catalyst ◽  
Catalyst System ◽  
Side Reactions ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Dehydrogenative Coupling ◽  
Carbon Carbon Bonds ◽  
Pseudo Halides ◽  
Direct Use

Construction of carbon–carbon bonds is one of the most essential tools in chemical synthesis. In the previously established cross-coupling reactions, pre-functionalized starting materials are employed usually in the form of arylor alkyl (pseudo)halides or their metallated derivatives. However, direct use of arenes and alkanes via a twofold oxidative C–H bond activation strategy to access chemoselective C(sp2 )‒C(sp3 ) cross-couplings is highly challenging due to the low reactivity of carbon–hydrogen (C–H) bonds and the difficulty in suppressing side reactions such as homocouplings. Herein, we present a copper-catalyzed cross-dehydrogenative coupling of perfluoroarenes with alkanes. Mechanistic information was obtained by combining experimental and computational studies to suggest that the optimal diketimine copper catalyst system plays a dual role to activate both sp3 and sp2 C‒H bonds.

scholarly journals Copper-Catalyzed Direct Alkylation of Perfluoroarenes with Hydrocarbons

2019 ◽  
Author(s):  
Weilong Xie ◽  
Joon Heo ◽  
Dongwook Kim ◽  
Sukbok Chang
Keyword(s):  
Bond Activation ◽  
Copper Catalyst ◽  
Catalyst System ◽  
Side Reactions ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Dehydrogenative Coupling ◽  
Carbon Carbon Bonds ◽  
Pseudo Halides ◽  
Direct Use

Construction of carbon–carbon bonds is one of the most essential tools in chemical synthesis. In the previously established cross-coupling reactions, pre-functionalized starting materials are employed usually in the form of arylor alkyl (pseudo)halides or their metallated derivatives. However, direct use of arenes and alkanes via a twofold oxidative C–H bond activation strategy to access chemoselective C(sp2 )‒C(sp3 ) cross-couplings is highly challenging due to the low reactivity of carbon–hydrogen (C–H) bonds and the difficulty in suppressing side reactions such as homocouplings. Herein, we present a copper-catalyzed cross-dehydrogenative coupling of perfluoroarenes with alkanes. Mechanistic information was obtained by combining experimental and computational studies to suggest that the optimal diketimine copper catalyst system plays a dual role to activate both sp3 and sp2 C‒H bonds.

The singlet excited state of BODIPY promoted aerobic cross-dehydrogenative-coupling reactions under visible light

2015 ◽  
Vol 51 (56) ◽  
pp. 11256-11259 ◽  
Author(s):  
Xu-Zhe Wang ◽  
Qing-Yuan Meng ◽  
Jian-Ji Zhong ◽  
Xue-Wang Gao ◽  
Tao Lei ◽  
...  
Keyword(s):  
Excited State ◽  
Visible Light ◽  
Bond Activation ◽  
Coupling Reactions ◽  
Singlet Excited State ◽  
Triplet Excited State ◽  
Dehydrogenative Coupling ◽  
First Time

We disclose for the first time that the singlet excited state (1PS*) of BODIPY rather than triplet excited state (3PS*) can drive C–H bond activation to form C–C and C–P bonds smoothly upon irradiation by visible light.

scholarly journals Iodine(III) promotes cross-dehydrogenative coupling of N-hydroxyphthalimide and unactivated C(sp3)–H bonds

2021 ◽  
Vol 4 (1) ◽  
Author(s):  
Fufang Wu ◽  
Xuanzhen Han ◽  
Xuejian Li ◽  
Xiaobao Shen ◽  
Chang Wang ◽  
...  
Keyword(s):  
Bond Activation ◽  
Coupling Reaction ◽  
Metal Catalyst ◽  
Coupling Reactions ◽  
Chemical Bonds ◽  
Reaction Conditions ◽  
Transition Metal Catalyst ◽  
Metal Free ◽  
Dehydrogenative Coupling ◽  
Ether Oxygen

AbstractCross-dehydrogenative coupling reactions provide a method to construct new chemical bonds by direct C–H activation without any pre-functionalization. Compared to functionalization of a C–H bond α- to ether oxygen, α- to carbonyl, or at a benzylic position, functionalization of unactivated hydrocarbons is difficult and often requires high temperatures, a transition-metal catalyst, or a superstoichiometric quantity of volatile, toxic, and explosive tert-butylhydroperoxide. Here, a cross-dehydrogenative C–O coupling reaction of N-hydroxyphthalimide with unactivated alkanes, nitriles, ethers, and thioethers has been realized by using iodobenzene diacetate as the radical initiator. The current protocol enables efficient functionalization of unactivated hydrocarbons and nitriles through inert C(sp3)–H bond activation under mild reaction conditions. O-substituted NHPI derivatives are generated in good yields under metal-free conditions.

Transition-Metal-Free Synthetic Strategies for the Cross-Coupling Reactions in Water: A Green Approach

2020 ◽  
Vol 07 ◽  
Author(s):  
Tanmay Chatterjee ◽  
Nilanjana Mukherjee
Keyword(s):  
Transition Metal ◽  
Organic Solvents ◽  
Aqueous Media ◽  
Cross Coupling ◽  
Transition Metal Catalysts ◽  
Synthetic Methods ◽  
Coupling Reactions ◽  
Organic Transformations ◽  
Green Approach ◽  
Dehydrogenative Coupling

Abstract: A natural driving force is always working behind the synthetic organic chemists towards the development of ‘green’ synthetic methodologies for the synthesis of useful classes of organic molecules having potential applications. The majority of the essential classes of organic transformations, including C-C and C-X (X = heteroatom) bond-forming crosscoupling reactions, cross dehydrogenative-coupling (CDC) mostly rely on the requirement of transition-metal catalysts and hazardous organic solvents. Hence, the scope in developing green synthetic strategies by avoiding the use of transitionmetal catalysts and hazardous organic solvents for those important and useful classes of organic transformations is very high. Hence, several attempts are made so far. Water being the most abundant, cheap, and green solvent in the world; numerous synthetic methods have been developed in an aqueous medium. In this review, the development of transitionmetal- free green synthetic strategies for various important classes of organic transformations such as C-C and C-X bondforming cross-coupling, cross dehydrogenative-coupling, and oxidative-coupling in an aqueous media is discussed.

C-H bond functionalization using Pd and Au supported catalysts with mechanistic insights of the active species

Synthesis ◽  
2021 ◽  
Author(s):  
Tamao Ishida ◽  
Zhenzhong Zhang ◽  
Haruno Murayama ◽  
Eiji Yamamoto ◽  
Makoto Tokunaga
Keyword(s):  
Aromatic Compounds ◽  
Reaction Mechanisms ◽  
Bond Activation ◽  
Supported Catalysts ◽  
Metal Catalysts ◽  
Active Species ◽  
Supported Metal Catalysts ◽  
Bond Functionalization ◽  
Bond Forming ◽  
Supported Metal

The C–H functionalization has been extensively studied as a direct C–C bond forming reaction with high atomic efficiency. The efforts have also been made on the reaction using supported catalysts, which are superior in terms of catalyst separation from the reaction mixture and reusability. In this review, an overview of the C–H functionalization reactions, especially for Pd and Au supported catalysts will be described. In particular, we discuss reaction mechanisms, active species, leaching, reusability, etc. 1 Introduction 2 Types of supported metal catalysts and their active species 3 Modes of C–H bond activation 4 Oxidative C–H C–H coupling of aryl compounds 5 C–H C–H coupling where one side is aromatic 6 C–H acylation of aromatic compounds and related reactions 7 Conclusion

Palladium-catalyzed synthesis of aromatic acids from carbon monoxide and aromatic compounds via the aromatic CH bond activation

1990 ◽  
Vol 385 (2) ◽  
pp. 297-306 ◽  
Author(s):  
Tetsuro Jintoku ◽  
Yuzo Fujiwara ◽  
Itaru Kawata ◽  
Tomio Kawauchi ◽  
Hiroshi Taniguchi
Keyword(s):  
Carbon Monoxide ◽  
Aromatic Compounds ◽  
Bond Activation ◽  
Aromatic Acids ◽  
Palladium Catalyzed
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