TEMPO-Mediated Cross-Dehydrogenative Coupling of Indoles and Imidazo[1,2-a]pyridines with Fluorinated Alcohols

<div><div><div><p>Covalently bonded organic monolayers play important roles in defining the solution processability, ambient stability, and electronic properties of two-dimensional (2D) materials such as Ge nanosheets (GeNSs); they also hold promise of providing avenues for the fabrication of future generation electronic and optical devices. Functionalization of GeNS normally involves surface moieties linked through covalent Ge−C bonds. In the present contribution we extend the scope of surface linkages to include Si−Ge bonding and present the first demonstration of heteronuclear dehydrocoupling of organosilanes to hydride-terminated GeNSs obtained from the deintercalation and exfoliation of CaGe2. We further exploit this new surface reactivity and demonstrated the preparation of directly bonded silicon quantum dot-Ge nanosheet hybrids.</p></div></div></div>

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

Current Green Chemistry ◽

10.2174/2213346107999201006193653 ◽

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.

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Ruthenium-catalyzed synthesis of N-substituted lactams by acceptorless dehydrogenative coupling of diols with primary amines

Chemical Communications ◽

10.1039/c9cc06339k ◽

2019 ◽

Vol 55 (82) ◽

pp. 12384-12387 ◽

Cited By ~ 3

Author(s):

Yanling Zheng ◽

Xufeng Nie ◽

Yang Long ◽

Li Ji ◽

Haiyan Fu ◽

...

Keyword(s):

Phosphine Ligand ◽

Primary Amines ◽

Dehydrogenative Coupling ◽

One Step

The first synthesis of N-substituted lactams via an acceptorless dehydrogenative coupling of diols with primary amines in one step was enabled by combining Ru3(CO)12 with a hybrid N-heterocyclic carbene–phosphine–phosphine ligand as the catalyst.

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On-Surface Synthesis of Chiral π-Conjugate Porphyrin Tapes by Substrate-Regulated Dehydrogenative Coupling

The Journal of Physical Chemistry C ◽

10.1021/acs.jpcc.9b06025 ◽

2019 ◽

Vol 123 (37) ◽

pp. 23007-23013 ◽

Cited By ~ 1

Author(s):

Feifei Xiang ◽

Yan Lu ◽

Zhongping Wang ◽

Huanxin Ju ◽

Gianluca Di Filippo ◽

...

Keyword(s):

Dehydrogenative Coupling

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Stereospecific radical polymerization of N -tert -butoxycarbonylacrylamide in the presence of fluorinated alcohols

Journal of Polymer Science Part A Polymer Chemistry ◽

10.1002/pola.24373 ◽

2010 ◽

Vol 48 (24) ◽

pp. 5718-5726 ◽

Cited By ~ 4

Author(s):

Tomohiro Hirano ◽

Ryosuke Yamaoka ◽

Takamasa Miyazaki ◽

Koichi Ute

Keyword(s):

Radical Polymerization ◽

Fluorinated Alcohols

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Introducing Catalysis to Undergraduate Chemistry Students: Testing a Ru–NHC Complex in the Selective Dehydrogenative Coupling of Hydrosilanes and Alcohols

Journal of Chemical Education ◽

10.1021/acs.jchemed.1c00032 ◽

2021 ◽

Author(s):

Andrés Mollar-Cuni ◽

Carmen Mejuto ◽

David Ventura-Espinosa ◽

Pilar Borja ◽

Jose A. Mata

Keyword(s):

Chemistry Students ◽

Undergraduate Chemistry ◽

Dehydrogenative Coupling

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A cross-dehydrogenative C(sp3)−H heteroarylation via photo-induced catalytic chlorine radical generation

Nature Communications ◽

10.1038/s41467-021-24280-9 ◽

2021 ◽

Vol 12 (1) ◽

Author(s):

Chia-Yu Huang ◽

Jianbin Li ◽

Chao-Jun Li

Keyword(s):

Hydrogen Atom ◽

Hydrogen Evolution ◽

Alkyl Radical ◽

Cobalt Catalyst ◽

Alkylation Reaction ◽

Hydrogen Atom Abstraction ◽

Dehydrogenative Coupling ◽

Radical Generation ◽

Limited Scope

AbstractHydrogen atom abstraction (HAT) from C(sp3)–H bonds of naturally abundant alkanes for alkyl radical generation represents a promising yet underexplored strategy in the alkylation reaction designs since involving stoichiometric oxidants, excessive alkane loading, and limited scope are common drawbacks. Here we report a photo-induced and chemical oxidant-free cross-dehydrogenative coupling (CDC) between alkanes and heteroarenes using catalytic chloride and cobalt catalyst. Couplings of strong C(sp3)–H bond-containing substrates and complex heteroarenes, have been achieved with satisfactory yields. This dual catalytic platform features the in situ engendered chlorine radical for alkyl radical generation and exploits the cobaloxime catalyst to enable the hydrogen evolution for catalytic turnover. The practical value of this protocol was demonstrated by the gram-scale synthesis of alkylated heteroarene with merely 3 equiv. alkane loading.

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Synthesis of N-alkoxyphthalimide derivatives via PIDA-promoted cross dehydrogenative coupling reaction

RSC Advances ◽

10.1039/d1ra00375e ◽

2021 ◽

Vol 11 (14) ◽

pp. 8051-8054

Author(s):

Rongxiang Chen ◽

Bing Liu ◽

Wenbo Li ◽

Kai-Kai Wang ◽

Changqing Miao ◽

...

Keyword(s):

Coupling Reaction ◽

Dehydrogenative Coupling ◽

Aryl Ketones ◽

High Yields

A cross dehydrogenative coupling reaction of aryl ketones with N-hydroxyphthalimide was realized. The reactions afforded a clean and facile access to diverse N-alkoxyphthalimide derivatives in high yields (up to 99%).

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