Construction of C–C Bond via C–N and C–O Cleavage

Synlett ◽  
2019 ◽  
Vol 31 (07) ◽  
pp. 635-640
Author(s):  
Xiaobo Pang ◽  
Rong-De He ◽  
Xing-Zhong Shu
Keyword(s):  
Organic Chemistry ◽  
Recent Work ◽  
Design Space ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Ammonium Salts ◽  
Synthetic Organic Chemistry ◽  
Benzyl Ammonium ◽  
Organic Halides ◽  
The Cross

The construction of a C–C bond is a center subject in synthetic organic chemistry. The cross-electrophile coupling has provided a powerful tool to forge the C–C bond. However, this process generally requires organic halides, which has severely restricted the design space for new reactions. Herein, we highlight our recent work on the coupling reaction between C–N and C–O electrophiles. This work demonstrates the possibility of construction of C–C bond via C–N and C–O cleavage. A number of reactions between benzyl ammoniums and vinyl acetates, aryl ammoniums and vinyl acetates, and benzyl ammoniums and aryl C–O electrophiles have been studied. We also disclosed that benzyl ammonium salts can be activated by low-valent nickel to be radicals.1 Introduction2 Cross-Coupling of C–N and C–O Electrophiles3 Summary and Outlook

Photoinduced Coupling Reaction of Diphenyl(2,4,6-trimethylbenzoyl)phosphine Oxide with Interelement Compounds: Application to the Synthesis of Thio- or Selenophosphinates

Synthesis ◽  
2017 ◽  
Vol 49 (16) ◽  
pp. 3558-3567 ◽  
Author(s):  
Shin-ichi Kawaguchi ◽  
Akiya Ogawa ◽  
Yuki Sato ◽  
Akihiro Nomoto
Keyword(s):  
Organic Chemistry ◽  
Phosphine Oxide ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Synthetic Organic Chemistry ◽  
Radical Initiator ◽  
Macromolecular Chemistry ◽  
Cross Coupling Reaction ◽  
Phosphorus Source ◽  
The Cross

Diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide (TMDPO) is a radical initiator widely used in the field of macromolecular chemistry, but not often applied in synthetic organic chemistry. We have focused­ on the use of TMDPO as a phosphorus source in reactions with different E – E compounds, where E – E represents a heteroatom–heteroatom­ bond, under photoirradiation. Interestingly, the cross-coupling reaction between TMDPO and disulfides or diselenides successfully affords thio- or selenophosphinates and thio- or selenoesters, respectively. The synthesis of series of thio- and selenophosphinates by this photoinduced cross-coupling reaction is demonstrated.

scholarly journals Recent Advances in the Applications of the Intramolecular Suzuki Cross-coupling Reaction in Cyclization and Heterocyclization: An Update

2020 ◽  
Vol 23 (22) ◽  
pp. 2469-2488 ◽  
Author(s):  
Majid M. Heravi ◽  
Masoumeh Malmir ◽  
Razieh Moradi
Keyword(s):  
Organic Chemistry ◽  
Boronic Acid ◽  
Heterocyclic Compounds ◽  
Aryl Halide ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Synthetic Organic Chemistry ◽  
Previous Review ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed

: The palladium-catalyzed reaction of aryl halide and boronic acid for the formation of C–C bonds so-called Suzuki–Miyaura cross-coupling reaction has many applications in Modern Synthetic Organic Chemistry. In 2013, we emphasized the applications of the intramolecular Suzuki cross-coupling reaction in cyclization and heterocyclization. Due to a plethora relevant papers appeared in the chemical literature, herein, we wish to cover by updating our previous review, the applications of the intramolecular Suzuki cross-coupling reaction in cyclization and heterocyclization leading to various homocyclic and heterocyclic compounds reported during a period of 2013 to 2018.

Pd-catalyzed desulfitative arylation of olefins by N-methoxysulfonamide

2022 ◽  
Author(s):  
Subhadra Ojha ◽  
Niranjan Panda
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Type Reaction ◽  
Cross Coupling Reaction ◽  
The Cross

A novel Pd-catalyzed protocol desulfitative Heck type reaction of N-methoxy aryl sulfonamides with alkenes was reported. The cross-coupling reaction was performed successfully with a variety of olefins to obtainaryl alkenes....

scholarly journals A DFT Study on FeI/FeII/FeIII Mechanism of the Cross-Coupling between Haloalkane and Aryl Grignard Reagent Catalyzed by Iron-SciOPP Complexes

Molecules ◽  
2020 ◽  
Vol 25 (16) ◽  
pp. 3612 ◽  
Author(s):  
Akhilesh Sharma ◽  
Masaharu Nakamura
Keyword(s):  
Density Functional ◽  
Molecular Mechanic ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Dft Study ◽  
Reaction Pathways ◽  
Hydrogen Elimination ◽  
Cross Coupling Reaction ◽  
The Cross ◽  
A Chain

To explore plausible reaction pathways of the cross-coupling reaction between a haloalkane and an aryl metal reagent catalyzed by an iron–phosphine complex, we examine the reaction of FeBrPh(SciOPP) 1 and bromocycloheptane employing density functional theory (DFT) calculations. Besides the cross-coupling, we also examined the competitive pathways of β-hydrogen elimination to give the corresponding alkene byproduct. The DFT study on the reaction pathways explains the cross-coupling selectivity over the elimination in terms of FeI/FeII/FeIII mechanism which involves the generation of alkyl radical intermediates and their propagation in a chain reaction manner. The present study gives insight into the detailed molecular mechanic of the cross-coupling reaction and revises the FeII/FeII mechanisms previously proposed by us and others.

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