Aluminum–Ligand Cooperative N–H Bond Activation and an Example of Dehydrogenative Coupling

2013 ◽  
Vol 135 (27) ◽  
pp. 9988-9990 ◽  
Author(s):  
Thomas W. Myers ◽  
Louise A. Berben
Keyword(s):  
Bond Activation ◽  
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.

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

scholarly journals NH4I-mediated sp3 C-H cross-dehydrogenative coupling of benzylamines with 2-methylquinoline for the synthesis of E-2-styrylquinolines

2021 ◽  
pp. 174751982110192
Author(s):  
Xue Li ◽  
Bin Huang ◽  
JiangWei Wang ◽  
YuanYuan Zhang ◽  
WeiBo Liao
Keyword(s):  
Efficient Method ◽  
Bond Activation ◽  
Metal Catalyst ◽  
Dehydrogenative Coupling ◽  
Plausible Mechanism

Without any metal catalyst, a simple and efficient method for the synthesis of E-2-styrylquinolines through sp3 C-H cross-dehydrogenative coupling of benzylamines with 2-methylquinolines mediated by NH4I under air is successfully developed. The oxidative olefination proceeded through deamination and sp3 C–H bond activation. A plausible mechanism is proposed for the construction of E-2-styrylquinolines.

Di-tert-butyl peroxide (DTBP) promoted dehydrogenative coupling: an expedient and metal-free synthesis of oxindoles via intramolecular C(sp2)–H and C(sp3)–H bond activation

RSC Advances ◽  
2015 ◽  
Vol 5 (85) ◽  
pp. 69119-69123 ◽  
Author(s):  
Biplab Mondal ◽  
Brindaban Roy
Keyword(s):  
Bond Activation ◽  
Metal Free ◽  
Tert Butyl ◽  
Dehydrogenative Coupling ◽  
Butyl Peroxide

An efficient di-tert-butyl peroxide (DTBP) promoted synthesis of oxindole has been developed. This methodology involves C(sp3)–H and C(sp2)–H bond activation under metal-free conditions.

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.

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