Cascade Reaction of Donor–Acceptor Cyclopropanes: Mechanistic Studies on Cycloadditions with Nitrosoarenes and cis-Diazenes

2016 ◽  
Vol 18 (12) ◽  
pp. 2922-2925 ◽  
Author(s):  
Tristan Chidley ◽  
Naresh Vemula ◽  
Cheryl A. Carson ◽  
Michael A. Kerr ◽  
Brian L. Pagenkopf
Keyword(s):  
Cascade Reaction ◽  
Mechanistic Studies ◽  
Donor Acceptor

ChemInform Abstract: Cascade Reaction of Donor-Acceptor Cyclopropanes: Mechanistic Studies on Cycloadditions with Nitrosoarenes and cis-Diazenes.

ChemInform ◽  
2016 ◽  
Vol 47 (44) ◽  
Author(s):  
Tristan Chidley ◽  
Naresh Vemula ◽  
Cheryl A. Carson ◽  
Michael A. Kerr ◽  
Brian L. Pagenkopf
Keyword(s):  
Cascade Reaction ◽  
Mechanistic Studies ◽  
Donor Acceptor

scholarly journals Halogen-bonding-promoted Photo-induced C–X Borylation of Aryl Halide using Phenol Derivatives

2022 ◽  
Author(s):  
Kazuki Matsuo ◽  
Eiji Yamaguchi ◽  
Akichika Itoh
Keyword(s):  
Functional Group ◽  
Aryl Halide ◽  
Halogen Bonding ◽  
Mechanistic Studies ◽  
Boronate Esters ◽  
Aryl Radicals ◽  
Phenol Derivatives ◽  
Mild Conditions ◽  
Donor Acceptor ◽  
Photo Induced Electron Transfer

This study investigates the photo-induced C–X borylation reaction of aryl halides by forming a halogen-bonding complex. The method employs 2-naphthol as a halogen-bonding acceptor and proceeds under mild conditions without a photoredox catalyst under 420 nm blue light irradiation. The method is highly chemoselective, broadly functional group tolerant, and provides concise access to corresponding boronate esters. Mechanistic studies reveal that forming the halogen-bonding complex between aryl halide and naphthol acts as an electron donor-acceptor complex to furnish aryl radicals through photo-induced electron transfer.

Radical-mediated multicomponent cascade reaction for the synthesis of azide-biindole derivatives

2021 ◽  
Author(s):  
Xiaoyu Liu ◽  
Kun He ◽  
Na Gao ◽  
Peiyun Jiang ◽  
Jun Lin ◽  
...  
Keyword(s):  
Free Radical ◽  
Cascade Reaction ◽  
Mechanistic Studies ◽  
One Pot

A radical-mediated, one-pot, multicomponent cascade reaction was developed for the synthesis of azide-biindole derivatives. Mechanistic studies demonstrated that the nitrogen-centred free radical was formed by the reaction of the heterocyclic...

scholarly journals Development of highly efficient platinum catalysts for hydroalkoxylation and hydroamination of unactivated alkenes

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Yali Zhou ◽  
Xingjun Xu ◽  
Hongwei Sun ◽  
Guanyu Tao ◽  
Xiao-Yong Chang ◽  
...  
Keyword(s):  
Catalytic System ◽  
Rational Design ◽  
Platinum Catalysts ◽  
High Reactivity ◽  
Structural Components ◽  
Mechanistic Studies ◽  
Mild Conditions ◽  
Naturally Occurring ◽  
Donor Acceptor ◽  
Type Intermediate

AbstractHydrofunctionalization, the direct addition of an X–H (e.g., X=O, N) bond across an alkene, is a desirable strategy to make heterocycles that are important structural components of naturally occurring molecules. Described here is the design and discovery of “donor–acceptor”-type platinum catalysts that are highly effective in both hydroalkoxylation and hydroamination of unactivated alkenes over a broad range of substrates under mild conditions. A number of alkene substitution patterns are accommodated, including tri-substituted, 1,1-disubstituted, (E)-disubstituted, (Z)-disubstituted and even mono-substituted double bonds. Detailed mechanistic investigations suggest a plausible pathway that includes an unexpected dissociation/re-association of the electron-deficient ligand to form an alkene-bound “donor–acceptor”-type intermediate. These mechanistic studies help understand the origins of the high reactivity exhibited by the catalytic system, and provide a foundation for the rational design of chiral catalysts towards asymmetric hydrofunctionalization reactions.

scholarly journals Mechanistic studies of 1,3-dipolar cycloadditions of bicyclic thioisomünchnones with alkenes. A computational rationale focused on donor–acceptor interactions

2018 ◽  
Vol 16 (18) ◽  
pp. 3438-3452 ◽  
Author(s):  
Juan García de la Concepción ◽  
Martín Ávalos ◽  
Pedro Cintas ◽  
José L. Jiménez ◽  
Mark E. Light
Keyword(s):  
Mechanistic Studies ◽  
Dipolar Cycloadditions ◽  
Donor Acceptor

Unlike monocyclic mesoionic dipoles, bicyclic thioisomünchnones provide high levels of regio- and stereoselection leading to heteroatom-rich polycycles.

Electrospray mass spectrometry for detailed mechanistic studies of a complex organocatalyzed triple cascade reaction

2011 ◽  
Vol 9 (4) ◽  
pp. 1047-1053 ◽  
Author(s):  
M. Wasim Alachraf ◽  
Peni P. Handayani ◽  
Matthias R. M. Hüttl ◽  
Christoph Grondal ◽  
Dieter Enders ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Electrospray Mass Spectrometry ◽  
Cascade Reaction ◽  
Mechanistic Studies

scholarly journals Development of Highly Efficient Platinum Catalysts for Hydroalkoxylation and Hydroamination of Unactivated Alkene

2020 ◽  
Author(s):  
Yali Zhou ◽  
Xingjun Xu ◽  
Hongwei Sun ◽  
Guanyu Tao ◽  
Xiaoyong Chang ◽  
...  
Keyword(s):  
Catalytic System ◽  
Rational Design ◽  
Platinum Catalysts ◽  
High Reactivity ◽  
Structural Components ◽  
Mechanistic Studies ◽  
Mild Conditions ◽  
Naturally Occurring ◽  
Donor Acceptor ◽  
Type Intermediate

Abstract Hydrofunctionalization, the direct additon of an X–H (e.g., X = O, N) bond across an alkene, is a desirable strategy to make heterocycles that are important structural components of naturally occurring molecules. Described here is the design and discovery of “donor–acceptor”-type platinum catalysts that are highly effective in both hydroalkoxylation and hydroamination of unactivated alkenes over a broad range of substrates under mild conditions. A number of alkene substitution patterns were accommodated, including tri-substituted, 1,1-disubstituted, (E)-disubstituted, (Z)-disubstituted and even mono-substituted double bonds. Detailed mechanistic investigations suggest a plausible pathway that includes an unexpected dissociation/re-association of the electron-deficient ligand to form an alkene-bound “donor–acceptor”-type intermediate. These mechanistic studies help understand the origins of the high reactivity exhibited by the catalytic system, and provide a foundation for the rational design of chiral catalysts towards asymmetric hydrofunctionalization reactions.

Metal-Free Generation of Phosphorus-Centered Radicals for the Synthesis of Phosphorus-Based Heterocycles: A Personal Account

Synthesis ◽  
2017 ◽  
Vol 49 (15) ◽  
pp. 3444-3452 ◽  
Author(s):  
Valentin Quint ◽  
Ludovik Noël-Duchesneau ◽  
Elodie Lagadic ◽  
Fabrice Morlet-Savary ◽  
Jacques Lalevée ◽  
...  
Keyword(s):  
Electron Paramagnetic Resonance ◽  
Short Review ◽  
Photoredox Catalysis ◽  
Mechanistic Studies ◽  
Personal Account ◽  
Paramagnetic Resonance ◽  
Metal Free ◽  
Donor Acceptor ◽  
Free Generation ◽  
Electron Paramagnetic

This short review describes our recent efforts to generate phosphorus-based radicals under metal-free conditions and their use as key intermediates for the synthesis of phosphorus-based heterocycles. In this regard, the synthesis of benzo[b]phosphole oxides and 6-phosphorylated phenanthridines will be reported. While the synthesis of the former lies in the use of photoredox catalysis, the latter have been obtained through the use of an electron donor–acceptor complex from the combination of diphenyliodonium ion with triethylamine. Mechanistic aspects of both reaction types are discussed based on detailed mechanistic studies including electron paramagnetic resonance, UV–vis spectroscopic, NMR and steady-state photolysis experiments.1 Introduction2 Photoredox Catalysis for the Generation of Phosphinoyl Radicals3 Generation of Phosphinoyl Radicals through the Formation of EDA Complexes4 Conclusions

scholarly journals Visible-light-mediated α-phosphorylation of N-aryl tertiary amines through the formation of electron-donor–acceptor complexes: synthetic and mechanistic studies

2019 ◽  
Vol 6 (1) ◽  
pp. 41-44 ◽  
Author(s):  
Valentin Quint ◽  
Nourhène Chouchène ◽  
Moheddine Askri ◽  
Jacques Lalevée ◽  
Annie-Claude Gaumont ◽  
...  
Keyword(s):  
Visible Light ◽  
Electron Donor ◽  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
Tertiary Amines ◽  
Mechanistic Studies ◽  
Donor Acceptor

A visible light-mediated photocatalyst-free approach for the oxidative α-CH functionalization of N-aryl tertiary amines with secondary phosphine oxides has been developed.

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